dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-52fd80fbaf8b482ba702acb847f8a77a | COC(=O)C(Oc1ccc(C)cc1)c1ccccc1Cl.O=C1CCC(=O)N1Br>>COC(=O)C(Oc1ccc(CBr)cc1)c1ccccc1Cl | CC1=CC=C(OC(C(=O)OC)C2=C(C=CC=C2)Cl)C=C1.BrN1C(CCC1=O)=O.CC(C)(C#N)N=NC(C)(C)C#N>>BrCC1=CC=C(OC(C(=O)OC)C2=C(C=CC=C2)Cl)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]([O:6][c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[Cl:21].O=C1CCC(=O)N1[Br:12]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][Br:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[Cl:21] | COC(=O)C(Oc1ccc(C)cc1)c1ccccc1Cl.O=C1CCC(=O)N1Br | COC(=O)C(Oc1ccc(CBr)cc1)c1ccccc1Cl | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(COc2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 73 | [{"value": 73.0, "product": "BrCC1=CC=C(OC(C(=O)OC)C2=C(C=CC=C2)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product of Example 3, Step B (0.2 g, 0.69 mmol), N-bromosuccinimide (117 mg, 166 mmol) and a catalytic amount of AIBN in 2 ml CCl4 was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo and chromatographed on silica gel (125×20 mm) eluting with 5% ethyl acetate in hexane. The prod... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)C(Oc1ccc(C)cc1)c1ccccc1Cl.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)C(Oc1ccc(CBr)cc1)c1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-64a0c4283173496db827ea2c2506a2c6 | O=C(O)c1ccc(CBr)cc1>>OCc1ccc(CBr)cc1 | BrCC1=CC=C(C(=O)O)C=C1.B.C1CCOC1>>BrCC1=CC=C(CO)C=C1 | O=[C:2]([OH:1])[c:3]1[cH:4][cH:5][c:6]([CH2:7][Br:8])[cH:9][cH:10]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Br:8])[cH:9][cH:10]1 | O=C(O)c1ccc(CBr)cc1 | OCc1ccc(CBr)cc1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 94.8 | [{"value": 94.0, "product": "BrCC1=CC=C(CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "BrCC1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | A suspension of 4-bromomethylbenzoic acid (5.04; 23.3 mmol) in THF (30 ml) was cooled to 0° C. and treated with borane/THF (35 mmol). The ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The excess borane was quenched with MeOH, and then with water, and the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | 0 | 1.5 | O=C(O)c1ccc(CBr)cc1>C1CCOC1>OCc1ccc(CBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4b757282b70e424b90883123caba82ec | CC(C)(C)[Si](C)(C)Cl.OCc1ccc(CBr)cc1>>CC(C)(C)[Si](C)(C)OCc1ccc(CBr)cc1 | BrCC1=CC=C(CO)C=C1.C(C)(C)N(C(C)C)CC.[Si](C)(C)(C(C)(C)C)Cl>>BrCC1=CC=C(C=C1)CO[Si](C)(C)C(C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][Br:15])[cH:16][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][Br:15])[cH:16][cH:17]1 | CC(C)(C)[Si](C)(C)Cl.OCc1ccc(CBr)cc1 | CC(C)(C)[Si](C)(C)OCc1ccc(CBr)cc1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[C:9]-[c:10] | 71 | [{"value": 71.0, "product": "BrCC1=CC=C(C=C1)CO[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of the product of Example 4 Step A, (4.44 g, 22.1 mmol) in CH2Cl2 was added N,N-diisopropylethyl amine (1.2 eq.) and 4-dimethylaminopyridine (0.1 eq.), and t-butyldimethylsilyl chloride (1.2 eq.). The mixture was stirred for 1.5 hours at room temperature, then concentrated in vacuo. The residue was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 1.5 | CC(C)(C)[Si](C)(C)Cl.OCc1ccc(CBr)cc1>CN(C1=CC=NC=C1)C.C(Cl)Cl>CC(C)(C)[Si](C)(C)OCc1ccc(CBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-02742acc49b343f1b44fb58c1729b32d | C=CCBr.CC=Cc1cc(C(=O)OC)ccc1O>>C=CCOc1ccc(C(=O)OC)cc1CC=C | OC1=C(C=C(C(=O)OC)C=C1)C=CC.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)C=1C=C(C(=O)OC)C=CC1OCC=C | Br[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]1[CH:15]=[CH:16][CH3:17]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]1[CH2:15][CH:16]=[CH2:17] | C=CCBr.CC=Cc1cc(C(=O)OC)ccc1O | C=CCOc1ccc(C(=O)OC)cc1CC=C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b8db7cf2479349c01ec3e2623a49a038f13350515245053930c5d0a350eba234 | bd3a5d23389eaded3b33b4829b9cbf393413c7c096b27add63b1070e4769b900 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[CH3;D1;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:7](-[CH2;D2;+0:6]-[CH;D2;+0:5]=[CH2;D1;+0:4]):[c:8] | 87 | [{"value": 87.0, "product": "C(C=C)C=1C=C(C(=O)OC)C=CC1OCC=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3.04 g (15.8 mmol) of methyl 4-hydroxy-3-propenylbenzoate (Example 42, Step B) was refluxed with anhydrous potassium carbonate (4.37 g, 2 equiv) and allyl bromide (3.5 mL, 2.5 equiv) in acetone overnight. The mixture was filtered through Celite and the filter cake was washed with more acetone and dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol.Allyl | Ether.Allyl.Allyl | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | C=CCBr.CC=Cc1cc(C(=O)OC)ccc1O>CC(=O)C>C=CCOc1ccc(C(=O)OC)cc1CC=C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3170c5d6164841af935791c864839bf7 | C=CCOc1ccc(C(=O)OC)cc1CC=C>>C=CCc1cc(C(=O)OC)cc(CC=C)c1O | C(C=C)C=1C=C(C(=O)OC)C=CC1OCC=C.ClC1=C(C=CC=C1)Cl.C(C)(=O)OCC>>OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C | [CH2:1]=[CH:2][CH2:3][O:17][c:16]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]1[CH2:13][CH:14]=[CH2:15]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]([CH2:13][CH:14]=[CH2:15])[c:16]1[OH:17] | C=CCOc1ccc(C(=O)OC)cc1CC=C | C=CCc1cc(C(=O)OC)cc(CC=C)c1O | null | null | CCCCCC | Miscellaneous | OtherReaction | f9046ab8287acad6d9b914f5f533866252d6845a323cc2516eb4a5b1de541a76 | 58578155da4647eafb0f18a2061753170490dc4f2b17890a513522e28d385731 | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[cH;D2;+0:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[C:10]=[C;D1;H2:11]):[c:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c;H0;D3;+0:6](-[CH2;D2;+0:9]-[C:10]=[C;D1;H2:11]):[c:7](-[OH;D1;+0:8]):[c:12] | 97 | [{"value": 97.0, "product": "OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Step A (3.2 g, 13.8 mmol) was refluxed in 1,2-dichlorobenzene for 3 days in the presence of a catalytic amount of BHT (10 mg). Flash column chromatography of the mixture using hexane and then 10% and 20% ethyl acetate in hexane afforded 3.1 g (97%) of the title compound.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Allyl | Aromatic alcohol.Allyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CCCCCC | null | null | C=CCOc1ccc(C(=O)OC)cc1CC=C>CCCCCC>C=CCc1cc(C(=O)OC)cc(CC=C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-41017e4fa30246a4918c64d6a34e9480 | C=CCc1cc(C(=O)OC)cc(CC=C)c1O.CC(C)(C)[Si](C)(C)Cl>>C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C | OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C.[Si](C)(C)(C(C)(C)C)Cl.C(C)N(CC)CC>>[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C | [CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]([CH2:13][CH:14]=[CH2:15])[c:16]1[OH:17].Cl[Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]([CH2:13][CH:14]=[CH2:15])[c:16]1[O:17][Si:18]([CH3:19])... | C=CCc1cc(C(=O)OC)cc(CC=C)c1O.CC(C)(C)[Si](C)(C)Cl | C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C | null | CN(C)C=1C=CN=CC1 | ClCCl | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 97.2 | [{"value": 97.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Step B (3.1 g, 13.36 mmol) was treated with tert-butyldimethylsilyl chloride (2.22 g, 1.1 equiv), triethylamine (3 mL) and DMAP (0.1 equiv) in dichloromethane overnight. The mixture was concentrated and flash chromatographed with 5% and then 10% ethyl acetate in hexane to furnish 4.5 g (97%) of the title... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.ClCCl | null | null | C=CCc1cc(C(=O)OC)cc(CC=C)c1O.CC(C)(C)[Si](C)(C)Cl>CN(C)C=1C=CN=CC1.ClCCl>C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1f275fee41654dd1ae6647f1d1d8064a | C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C>>CCCc1cc(C(=O)OC)cc(CCC)c1O[Si](C)(C)C(C)(C)C | [Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CC=C)CC=C.[H][H]>>[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CCC)CCC | [CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]([CH2:13][CH:14]=[CH2:15])[c:16]1[O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]([CH2:13][CH2:14][CH3:15])[c:16]1[O:17][Si:18]([CH3:19])([CH... | C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C | CCCc1cc(C(=O)OC)cc(CCC)c1O[Si](C)(C)C(C)(C)C | null | null | C(C)O | Reduction | OtherReaction | f69b32ec19736437d6567a39731061f512e8e67ea9301cdcf93f07d7793003c3 | d69deccbf6585965088073408ee5be8b8c3152f4b9c3604883a5d86aa3bdd693 | c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4].[CH2;D1;+0:5]=[CH;D2;+0:6]-[C:7]-[c:8]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[C:7]-[c:8] | 90 | [{"value": 90.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CCC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5.0 g (14.45 mmol) of the product of Step C in 250 mL ethanol containing 5% Rh/C (0.25 g) was shaken under a 40 psi pressure of hydrogen. Upon completion of reduction, the mixture was filtered through Celite, the filter cake was washed with methanol and dichloromethane. Removal of solvents afforded 4.55 g... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | null | c1ccccc1 | null | C(C)O | null | null | C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C>C(C)O>CCCc1cc(C(=O)OC)cc(CCC)c1O[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fba0cb9fb1b145a1af2f772c0db3ce3a | CCCc1cc(C(=O)OC)cc(CCC)c1O[Si](C)(C)C(C)(C)C>>CCCc1cc(CO)cc(CCC)c1O[Si](C)(C)C(C)(C)C | C(C)(=O)OCC.Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C(=O)OC)C=C1CCC)CCC>>[Si](C)(C)(C(C)(C)C)OC1=C(C=C(CO)C=C1CCC)CCC | CO[C:7]([c:6]1[cH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:14]([O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[c:10]([CH2:11][CH2:12][CH3:13])[cH:9]1)=[O:8]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]([CH2:11][CH2:12][CH3:13])[c:14]1[O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([... | CCCc1cc(C(=O)OC)cc(CCC)c1O[Si](C)(C)C(C)(C)C | CCCc1cc(CO)cc(CCC)c1O[Si](C)(C)C(C)(C)C | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(CO)C=C1CCC)CCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | Lithium aluminum hydride (9 mL of a 1M solution in THF) was added cautiously to a solution of the product of Step D at 0° C., and the reaction mixture was stirred overnight. Ethyl acetate was added to the mixture, cooled to 0° C. and treated with cold 1N HCl. After separating the organic phase, the aqueous phase was ex... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | 0 | 8 | CCCc1cc(C(=O)OC)cc(CCC)c1O[Si](C)(C)C(C)(C)C>C1CCOC1>CCCc1cc(CO)cc(CCC)c1O[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f7c11daffec247348ae0459b122a7bd7 | CC1(C)CCCC1=O.O=Cc1ccc(Cl)cc1>>CC1(C)CCC(=Cc2ccc(Cl)cc2)C1=O | [OH-].[Na+].CC1(C(CCC1)=O)C.ClC1=CC=C(C=O)C=C1>>CC1(C(C(CC1)=CC1=CC=C(C=C1)Cl)=O)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][C:15]1=[O:16].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[CH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[C:15]1=[O:16] | CC1(C)CCCC1=O.O=Cc1ccc(Cl)cc1 | CC1(C)CCC(=Cc2ccc(Cl)cc2)C1=O | null | null | C(C)O | C-C Coupling | Aldol condensation | b57e203499046e3d3a056245b7f7f1438c7b88113257c8f40be758e4b3ca4e53 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1CCCC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 59.7 | [{"value": 59.7, "product": "CC1(C(C(CC1)=CC1=CC=C(C=C1)Cl)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 100 ml of a 10% aqueous solution of sodium hydroxide were added to a mixture of 10 g of 2,2-dimethylcyclopentanone and 13.8 g of 4-chlorobenzaldehyde in 100 ml of ethanol at 0° C. After 30 minutes, a thick slurry was filtered off and the solid washed and then dried. 12.5 g of 2,2-dimethyl-5-(4-chlorobenzylidene)-1-cycl... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | C1CCCC1 | C1CCCC1 | C1CCCC1.c1ccccc1 | HO- | C(C)O | null | 0.5 | CC1(C)CCCC1=O.O=Cc1ccc(Cl)cc1>C(C)O>CC1(C)CCC(=Cc2ccc(Cl)cc2)C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eedbb5551d384a5eb7e05d29c0ad602c | N#Cc1ccc(C(=O)c2cncs2)cc1>>C=C(c1ccc(C#N)cc1)c1cncs1 | C(CCC)[Li].C(#N)C1=CC=C(C(=O)C2=CN=CS2)C=C1.C(C)(=O)OCC>>C(#N)C1=CC=C(C=C1)C(=C)C1=CN=CS1 | O=[C:2]([c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9][cH:10]1)[c:11]1[cH:12][n:13][cH:14][s:15]1>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9][cH:10]1)[c:11]1[cH:12][n:13][cH:14][s:15]1 | N#Cc1ccc(C(=O)c2cncs2)cc1 | C=C(c1ccc(C#N)cc1)c1cncs1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CCOCC.CCCCCC | Functional Group Interconversion | OtherReaction | 77e55b8d58229cdaddbfef811692215b45ee4124fec87c1aa9c0e735816099ed | f395a9efbb80a99833acb686d4944d4880257993d074f4e04e21822999af09fe | C=C(c1ccccc1)c1cncs1 | O=[C;H0;D3;+0:1](-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1)-[c:7](:[c:8]):[c:9]>>[C;D1;H2:10]=[C;H0;D3;+0:1](-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1)-[c:7](:[c:8]):[c:9] | null | [] | null | null | 1.5 | HOUR | 714 mg of methyltriphenylphosphonium bromide are introduced into 6.7 ml of ether, and 0.973 ml of 1.6M n-butyllithium in hexane is added at 7°. The orange suspension is stirred at the same temperature for 1.5 hours and then reacted with a suspension, cooled to 7°, of 5-(4-cyanobenzoyl)-thiazole (Example 8a) in 3 ml of ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | null | null | c1ccccc1.c1cscn1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC.CCCCCC | null | 1.5 | N#Cc1ccc(C(=O)c2cncs2)cc1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC.CCCCCC>C=C(c1ccc(C#N)cc1)c1cncs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1b56fb4841074048a0f465a62bb0c8bb | OC1(c2ccns2)CCCc2cc(Cl)ccc21>>Clc1ccc2c(c1)CCC=C2c1ccns1 | S(=O)(Cl)Cl.ClC=1C=C2CCCC(C2=CC1)(C1=CC=NS1)O>>ClC=1C=C2CCC=C(C2=CC1)C1=CC=NS1 | O[C:11]1([c:12]2[cH:13][cH:14][n:15][s:16]2)[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:7][c:6]2[CH2:8][CH2:9][CH2:10]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][CH:10]=[C:11]2[c:12]1[cH:13][cH:14][n:15][s:16]1 | OC1(c2ccns2)CCCc2cc(Cl)ccc21 | Clc1ccc2c(c1)CCC=C2c1ccns1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 55de719a68f8efde968ccdcfe54c921765e82cad5ee57c0bae7adf2d5c6460b3 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(c2ccns2)c2ccccc2CC1 | O-[C;H0;D4;+0:1]1(-[c:2]2:[#16;a:3]:[#7;a:4]:[c:5]:[c:6]:2)-[CH2;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[c:12]:[c:11]1:[c:10]-[C:9]-[C:8]-[CH;D2;+0:7]=[C;H0;D3;+0:1]-1-[c:2]1:[#16;a:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | 1.5 | HOUR | 0.072 ml of thionyl chloride is added at room temperature to a solution of 132 mg of 6-chloro-1-hydroxy-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene (Example 12) in 0.45 ml of benzene, and the mixture is then stirred at 75° for 1.5 hours. The mixture is concentrated under reduced pressure, 0.156 ml of morpholine is... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1.c1cnsc1 | HO- | C1=CC=CC=C1 | null | 1.5 | OC1(c2ccns2)CCCc2cc(Cl)ccc21>C1=CC=CC=C1>Clc1ccc2c(c1)CCC=C2c1ccns1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9d47938a1fd34975a35c304222ad9c98 | N#Cc1ccc2c(c1)CCCC2(O)c1ccns1>>N#Cc1ccc2c(c1)CCC=C2c1ccns1 | C(#N)C=1C=C2CCCC(C2=CC1)(C1=CC=NS1)O.S(=O)(Cl)Cl.N1CCOCC1>>C(#N)C=1C=C2CCC=C(C2=CC1)C1=CC=NS1 | O[C:12]1([c:13]2[cH:14][cH:15][n:16][s:17]2)[c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:8][c:7]2[CH2:9][CH2:10][CH2:11]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]=[C:12]2[c:13]1[cH:14][cH:15][n:16][s:17]1 | N#Cc1ccc2c(c1)CCCC2(O)c1ccns1 | N#Cc1ccc2c(c1)CCC=C2c1ccns1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 55de719a68f8efde968ccdcfe54c921765e82cad5ee57c0bae7adf2d5c6460b3 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(c2ccns2)c2ccccc2CC1 | O-[C;H0;D4;+0:1]1(-[c:2]2:[#16;a:3]:[#7;a:4]:[c:5]:[c:6]:2)-[CH2;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[c:12]:[c:11]1:[c:10]-[C:9]-[C:8]-[CH;D2;+0:7]=[C;H0;D3;+0:1]-1-[c:2]1:[#16;a:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | Analogously to Example 13, 92 mg of 6-cyano-1-hydroxy-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene (Example 15) and 0.051 ml of thionyl chloride in 0.32 of benzene, with the subsequent addition of 0.112 ml of morpholine, are converted into the crude title compound, which is purified by column chromatography (SiO2, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1.c1cnsc1 | HO- | C1=CC=CC=C1 | null | null | N#Cc1ccc2c(c1)CCCC2(O)c1ccns1>C1=CC=CC=C1>N#Cc1ccc2c(c1)CCC=C2c1ccns1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8cd34d005b784e35943429391df8f304 | CC1(C)c2ccccc2S(=O)(=O)N1F.N#Cc1ccc2c(c1)CCCC2c1ccns1>>N#Cc1ccc2c(c1)CCCC2(F)c1ccns1 | C(C)(C)[N-]C(C)C.[Li+].FN1S(C2=C(C1(C)C)C=CC=C2)(=O)=O.C(#N)C=1C=C2CCCC(C2=CC1)C1=CC=NS1>>C(#N)C=1C=C2CCCC(C2=CC1)(C1=CC=NS1)F | CC1(C)c2ccccc2S(=O)(=O)N1[F:13].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][CH:12]2[c:14]1[cH:15][cH:16][n:17][s:18]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][C:12]2([F:13])[c:14]1[cH:15][cH:16][n:17][s:18]1 | CC1(C)c2ccccc2S(=O)(=O)N1F.N#Cc1ccc2c(c1)CCCC2c1ccns1 | N#Cc1ccc2c(c1)CCCC2(F)c1ccns1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | cc2ef0e0069a36420df916441cd485b3d799f2d83abf274c461dfd3ce545b517 | b9b7285d4c1e0345324067c8d83a9041d547a68825c14be4f5d3ec2bee6dd1ea | c1ccc2c(c1)CCCC2c1ccns1 | C-C1(-C)-N(-[F;H0;D1;+0:1])-S(=O)(=O)-c2:c:c:c:c:c:2-1.[C:2]-[C:3]-[CH;D3;+0:4](-[c:5]1:[#16;a:6]:[#7;a:7]:[c:8]:[c:9]:1)-[c:10](:[c:11]):[c:12]>>[C:2]-[C:3]-[C;H0;D4;+0:4](-[F;H0;D1;+0:1])(-[c:5]1:[#16;a:6]:[#7;a:7]:[c:8]:[c:9]:1)-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | 6-Cyano-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene (Example 26) is converted into the carbanion by treatment with lithium diisopropylamide in THF at -78° and then reacted with N-fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzothiazole-1,1-dioxide. The reaction mixture is allowed to warm to room temperature and is worked... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Tertiary halide | c1ccc2c(c1)CNS2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cnsc1 | HO- | C1CCOC1 | null | null | CC1(C)c2ccccc2S(=O)(=O)N1F.N#Cc1ccc2c(c1)CCCC2c1ccns1>C1CCOC1>N#Cc1ccc2c(c1)CCCC2(F)c1ccns1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fc328861075c4601a239c2cf487b943a | BrCCCc1ccccc1.N#CCc1ccc(Cl)cc1>>N#CC(CCCc1ccccc1)c1ccc(Cl)cc1 | [OH-].[Na+].CS(=O)C.ClC1=CC=C(C=C1)CC#N.BrCCCC1=CC=CC=C1>>ClC1=CC=C(C=C1)C(C#N)CCCC1=CC=CC=C1 | Br[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[N:1]#[C:2][CH2:3][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[N:1]#[C:2][CH:3]([CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | BrCCCc1ccccc1.N#CCc1ccc(Cl)cc1 | N#CC(CCCc1ccccc1)c1ccc(Cl)cc1 | null | null | O | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(CCCCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[N;D1;H0:4]#[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6](-[C:5]#[N;D1;H0:4])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | 2 ml of an aqueous sodium hydroxide (1.08 g) solution was added to a 10 ml solution of dimethylsulfoxide containing 1.0 g (6.6 mmole) of 4-chlorophenylacetonitrile and 1.3 g (6.6 mmole) of 1-bromo-3-phenylpropane at room temperature. After stirring for 2 hours under the same conditions, water was added to the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1 | HBr | O | null | null | BrCCCc1ccccc1.N#CCc1ccc(Cl)cc1>O>N#CC(CCCc1ccccc1)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9eff2be66d41411fafc7473e558a11ff | CN=C=S.N#CC(CCCc1ccccc1)c1ccc(Cl)cc1>>CNC(=S)C(C#N)(CCCc1ccccc1)c1ccc(Cl)cc1 | CC(C)([O-])C.[K+].O1CCCC1.CN=C=S.O1CCCC1.ClC1=CC=C(C=C1)C(C#N)CCCC1=CC=CC=C1.O1CCCC1>>CNC(C(CCCC1=CC=CC=C1)(C#N)C1=CC=C(C=C1)Cl)=S | [CH3:1][N:2]=[C:3]=[S:4].[CH:5]([C:6]#[N:7])([CH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][NH:2][C:3](=[S:4])[C:5]([C:6]#[N:7])([CH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][c... | CN=C=S.N#CC(CCCc1ccccc1)c1ccc(Cl)cc1 | CNC(=S)C(C#N)(CCCc1ccccc1)c1ccc(Cl)cc1 | null | null | O | C-C Coupling | OtherReaction | 706800b195a9d2df066382118f8bcd8922999484f5b39f0d82e9ea3fbde77d09 | d7b724a65bc106dc7a946f2e701375e84e0b4f4ba3281bc66eb872412d96192b | c1ccc(CCCCc2ccccc2)cc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[S;D1;H0:4].[C:5]-[C:6]-[CH;D3;+0:7](-[C:8]#[N;D1;H0:9])-[c:10](:[c:11]):[c:12]>>[C:5]-[C:6]-[C;H0;D4;+0:7](-[C:8]#[N;D1;H0:9])(-[C;H0;D3;+0:3](=[S;D1;H0:4])-[NH;D2;+0:2]-[C;D1;H3:1])-[c:10](:[c:11]):[c:12] | 52.6 | [{"value": 52.4, "product": "CNC(C(CCCC1=CC=CC=C1)(C#N)C1=CC=C(C=C1)Cl)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.6, "product": "CNC(C(CCCC1=CC=CC=C1)(C#N)C1=CC=C(C=C1)Cl)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a tetrahydrofuran solution containing 1.78 g (6.6 mmole) of 2-(4-chlorophenyl)-5-phenylvaleronitrile was added a tetrahydrofuran solution containing 0.77 g (6.9 mmole) of potassium tert-butoxide at 0° C. After stirring for 30 minutes, a tetrahydrofuran solution containing 0.5 g (6.8 mmol) of methyl isothiocyanate wa... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thioamide | null | null | c1ccccc1.c1ccccc1 | null | O | null | 0.5 | CN=C=S.N#CC(CCCc1ccccc1)c1ccc(Cl)cc1>O>CNC(=S)C(C#N)(CCCc1ccccc1)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-97a71ab8b30846a79c74a25e489cdea9 | CN=C=S.N#CC(Cc1ccccc1)c1ccc(Cl)cc1>>CNC(=S)C(C)(C#N)c1ccc(Cl)cc1 | CN=C=S.C(C)(C)[N-]C(C)C.[Li+].ClC1=CC=C(C(CC2=CC=CC=C2)C#N)C=C1>>CNC(C(C)(C#N)C1=CC=C(C=C1)Cl)=S | [CH3:1][N:2]=[C:3]=[S:4].c1ccc([CH2:6][CH:5]([C:7]#[N:8])[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)cc1>>[CH3:1][NH:2][C:3](=[S:4])[C:5]([CH3:6])([C:7]#[N:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | CN=C=S.N#CC(Cc1ccccc1)c1ccc(Cl)cc1 | CNC(=S)C(C)(C#N)c1ccc(Cl)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 3523ebed15ce4cbabd481d9e2f67bd0a716a617d8f5732db2088b432d7db5aec | d7b724a65bc106dc7a946f2e701375e84e0b4f4ba3281bc66eb872412d96192b | c1ccccc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[S;D1;H0:4].[N;D1;H0:5]#[C:6]-[CH;D3;+0:7](-[CH2;D2;+0:8]-c1:c:c:c:c:c:1)-[c:9](:[c:10]):[c:11]>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[S;D1;H0:4])-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[C:6]#[N;D1;H0:5])-[c:9](:[c:10]):[c:11] | 31.4 | [{"value": 31.4, "product": "CNC(C(C)(C#N)C1=CC=C(C=C1)Cl)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.4, "product": "CNC(C(C)(C#N)C1=CC=C(C=C1)Cl)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a 10 ml tetrahydrofuran solution containing 1.00 g (6 mmole) of 4-chlorophenylmethylbenzylcyanide was added a 3.2 ml tetrahydrofuran solution containing 2 M of lithium diisopropylamide at -60° C. After stirring for 30 minutes under the same conditions, a 5 ml tetrahydrofuran solution containing 0.44 g (6 mmol) of me... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thioamide | c1ccccc1 | null | c1ccccc1 | Other | O1CCCC1 | null | 0.5 | CN=C=S.N#CC(Cc1ccccc1)c1ccc(Cl)cc1>O1CCCC1>CNC(=S)C(C)(C#N)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5feff57a661c408cb8eed94f0365db77 | CC(=O)c1ccc(C#N)cc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>N#CCCc1ccc(C#N)cc1 | CC(C)([O-])C.[K+].COCCOC.C(C)(=O)C1=CC=C(C#N)C=C1.C1(=CC=C(C=C1)S(=O)(=O)C[N+]#[C-])C>>C(#N)C1=CC=C(C=C1)CCC#N | O=[C:4]([CH3:3])[c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1.Cc1ccc(S(=O)(=O)C[N+:1]#[C-:2])cc1>>[N:1]#[C:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1 | CC(=O)c1ccc(C#N)cc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | N#CCCc1ccc(C#N)cc1 | null | null | C(C)O | C-C Coupling | OtherReaction | caa2c50daccf377c72c7546f4bc22799915e983ed5490a236776651a7260196b | b8a136d570ce816857081cb8ba2c1f21405f4d266911b27f92b17bc69608f020 | c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-C-[N+;H0;D2:1]#[C-;H0;D1:2]):c:c:1.O=[C;H0;D3;+0:3](-[CH3;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[c:5](:[c:6]):[c:7] | 70.4 | [{"value": 70.4, "product": "C(#N)C1=CC=C(C=C1)CCC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "C(#N)C1=CC=C(C=C1)CCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 1.40 g (1.25 mmole) of potassium tert-butoxide was added to a 17 ml ethylene glycol dimethyl ether solution containing 0.73 g (5 mmole) of 4-acetylbenzonitrile, 0.5 ml of ethanol and 1.27 g (6.5 mmole) of p-toluenesulfonylmethylisocyanide under ice-cooling; then the mixture was stirred at room temperature for 0.5 hour ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Isocyanide | Nitrile | c1ccccc1 | null | c1ccccc1 | TsOH.HO- | C(C)O | null | 0.5 | CC(=O)c1ccc(C#N)cc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>C(C)O>N#CCCc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-274c947a2e0049788e83af50650c54b2 | CC(C#N)c1ccc(-n2ccnc2)cc1.CN=C=S>>CNC(=S)C(C)(C#N)c1ccc(-n2ccnc2)cc1 | CC(C)([O-])C.[K+].O1CCCC1.CN=C=S.O1CCCC1.N1(C=NC=C1)C1=CC=C(C=C1)C(C#N)C.O1CCCC1>>CNC(C(C)(C#N)C1=CC=C(C=C1)N1C=NC=C1)=S | [CH:5]([CH3:6])([C:7]#[N:8])[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][n:16][cH:17]2)[cH:18][cH:19]1.[CH3:1][N:2]=[C:3]=[S:4]>>[CH3:1][NH:2][C:3](=[S:4])[C:5]([CH3:6])([C:7]#[N:8])[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][n:16][cH:17]2)[cH:18][cH:19]1 | CC(C#N)c1ccc(-n2ccnc2)cc1.CN=C=S | CNC(=S)C(C)(C#N)c1ccc(-n2ccnc2)cc1 | null | null | O | C-C Coupling | OtherReaction | 706800b195a9d2df066382118f8bcd8922999484f5b39f0d82e9ea3fbde77d09 | d7b724a65bc106dc7a946f2e701375e84e0b4f4ba3281bc66eb872412d96192b | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[C:3]#[N;D1;H0:4])-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[S;D1;H0:11]>>[C;D1;H3:8]-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[S;D1;H0:11])-[C;H0;D4;+0:2](-[C;D1;H3:1])(-[C:3]#[N;D1;H0:4])-[c:5](:[c:6]):[c:7] | 54.4 | [{"value": 54.0, "product": "CNC(C(C)(C#N)C1=CC=C(C=C1)N1C=NC=C1)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "CNC(C(C)(C#N)C1=CC=C(C=C1)N1C=NC=C1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a 10 ml tetrahydrofuran solution containing 1.00 g (5.1 mmole) of 2-[4-(1-imidazolyl)-phenyl]propionitrile was added a 10 ml tetrahydrofuran solution containing 0.69 g (6.2 mmole) of potassium tert-butoxide at 0 C. After stirring for 0.5 hour, a 5 ml tetrahydrofuran solution containing 0.45 g (6.2 mmole) of methyl i... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thioamide | null | null | c1ccccc1.c1c[nH]cn1 | null | O | null | 0.5 | CC(C#N)c1ccc(-n2ccnc2)cc1.CN=C=S>O>CNC(=S)C(C)(C#N)c1ccc(-n2ccnc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5a2e0fa900e849bd934831b9f151892d | Cc1c(CCC(=O)O)[nH]c2ccc(F)cc12.ClCc1ccc(-n2ccnc2)cc1>>Cc1c(CCC(=O)O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12 | O.[H-].[Na+].FC=1C=C2C(=C(NC2=CC1)CCC(=O)O)C.Cl.ClCC1=CC=C(C=C1)N1C=NC=C1>>FC=1C=C2C(=C(N(C2=CC1)CC1=CC=C(C=C1)N1C=NC=C1)CCC(=O)O)C | [CH3:1][c:2]1[c:3]([CH2:4][CH2:5][C:6](=[O:7])[OH:8])[nH:9][c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]12.Cl[CH2:10][c:11]1[cH:12][cH:13][c:14](-[n:15]2[cH:16][cH:17][n:18][cH:19]2)[cH:20][cH:21]1>>[CH3:1][c:2]1[c:3]([CH2:4][CH2:5][C:6](=[O:7])[OH:8])[n:9]([CH2:10][c:11]2[cH:12][cH:13][c:14](-[n:15]3[cH:16][cH:17][... | Cc1c(CCC(=O)O)[nH]c2ccc(F)cc12.ClCc1ccc(-n2ccnc2)cc1 | Cc1c(CCC(=O)O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)ccn2Cc1ccc(-n2ccnc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 10.4 | [{"value": 10.4, "product": "FC=1C=C2C(=C(N(C2=CC1)CC1=CC=C(C=C1)N1C=NC=C1)CCC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 60 | MINUTE | A solution of 198 mg of 5-fluoro-3-methyl-1H-indole-2-propanoic acid in 20 ml of dry DMF is cooled at 0° C., and treated with 155 mg of 55% NaH. The reaction mixture is stirred for 60 minutes at 0° C., then 307 mg of 1-[4-(chloro-methyl)phenyl]-1H-imidazole hydrochloride are added portionwise under nitrogen at 0° C. Af... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1c[nH]cn1.c1ccc2[nH]ccc2c1 | HCl | CN(C)C=O | 0 | 1 | Cc1c(CCC(=O)O)[nH]c2ccc(F)cc12.ClCc1ccc(-n2ccnc2)cc1>CN(C)C=O>Cc1c(CCC(=O)O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ce2094f8a0e9499fa6e6eca4f823126b | Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12>>Cc1c(CCC(=O)O)[nH]c2ccc(F)cc12 | FC=1C=C2C(=C(NC2=CC1)CCC(=O)OC(C)C)C.[OH-].[Na+].CO>>FC=1C=C2C(=C(NC2=CC1)CCC(=O)O)C | CC(C)[O:8][C:6]([CH2:5][CH2:4][c:3]1[c:2]([CH3:1])[c:16]2[c:10]([nH:9]1)[cH:11][cH:12][c:13]([F:14])[cH:15]2)=[O:7]>>[CH3:1][c:2]1[c:3]([CH2:4][CH2:5][C:6](=[O:7])[OH:8])[nH:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]12 | Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12 | Cc1c(CCC(=O)O)[nH]c2ccc(F)cc12 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ccc2c1 | C-C(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 102 | [{"value": 102.0, "product": "FC=1C=C2C(=C(NC2=CC1)CCC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of isopropyl 5-fluoro-3-methyl-1H-indole-2-propanoate (0.42 g),1N sodiumhydroxide (6.3 ml) and methanol (20 ml) are stirred at room temperature for 4 hours. The reaction mixture is poured into water, washed with methylene chloride, acidified with 1N HCl and extracted with methylene chloride. The organic layer... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | O | null | 4 | Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12>O>Cc1c(CCC(=O)O)[nH]c2ccc(F)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7032a768e4ff40098e40773662a0af2f | CCOC(=O)CCC(=O)CC.NNc1ccc(F)cc1>>Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12 | C(=O)(O)[O-].[Na+].Cl.FC1=CC=C(C=C1)NN.O=C(CCC(=O)OCC)CC.OS(=O)(=O)O>>FC=1C=C2C(=C(NC2=CC1)CCC(=O)OC(C)C)C | O=[C:3]([CH2:2][CH3:1])[CH2:4][CH2:5][C:6](=[O:7])[O:8][CH2:9][CH3:11].N[NH:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[c:3]([CH2:4][CH2:5][C:6](=[O:7])[O:8][CH:9]([CH3:10])[CH3:11])[nH:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]12 | CCOC(=O)CCC(=O)CC.NNc1ccc(F)cc1 | Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12 | null | null | CC(C)O | Aromatic Heterocycle Formation | OtherReaction | 78c96ede94646b1fadcb280844f4784088300d2e9acddb79df4c23e633659338 | b53f059516cefb165365dd6c7f027fb5592e4735648f83ddbddba0368d3facf4 | c1ccc2[nH]ccc2c1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[CH2;D2;+0:13]-[C;D1;H3:14])-[CH2;D2;+0:15]-[C;D1;H3:16]>>[C;D1;H3:17]-[CH;D3;+0:13](-[C;D1;H3:14])-[#8:12]-[C:10](=[O;D1;H0:11])-[C:9]-[C:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]... | null | [] | null | null | null | null | A mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (1.03 g), ethyl 4-oxo-hexanoate (1.0 g), 2-propanol (25 ml) and H2SO4 is refluxed under nitrogen for 9 hours. After cooling the mixture is poured into a aqueous solution of NaHCO3, extracted with AcOEt and evaporated to dryness to yield 1.45 g of isopropyl 5-fluoro... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester | Ester | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | CC(C)O | null | null | CCOC(=O)CCC(=O)CC.NNc1ccc(F)cc1>CC(C)O>Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9a8ff7f9ad0e479a86acac8c6fa85654 | Cc1c(CCC(=O)O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12.N>>Cc1c(CCC(N)=O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12 | FC=1C=C2C(=C(N(C2=CC1)CC1=CC=C(C=C1)N1C=NC=C1)CCC(=O)O)C.O=S(Cl)Cl.N>>FC=1C=C2C(=C(N(C2=CC1)CC1=CC=C(C=C1)N1C=NC=C1)CCC(=O)N)C | O[C:6]([CH2:5][CH2:4][c:3]1[c:2]([CH3:1])[c:28]2[c:22]([n:9]1[CH2:10][c:11]1[cH:12][cH:13][c:14](-[n:15]3[cH:16][cH:17][n:18][cH:19]3)[cH:20][cH:21]1)[cH:23][cH:24][c:25]([F:26])[cH:27]2)=[O:8].[NH3:7]>>[CH3:1][c:2]1[c:3]([CH2:4][CH2:5][C:6]([NH2:7])=[O:8])[n:9]([CH2:10][c:11]2[cH:12][cH:13][c:14](-[n:15]3[cH:16][cH:17... | Cc1c(CCC(=O)O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12.N | Cc1c(CCC(N)=O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12 | null | null | CN(C)C=O | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccc2c(c1)ccn2Cc1ccc(-n2ccnc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | null | [] | null | null | 6 | HOUR | A suspension of 5-fluoro-1-[[4-(1H-imidazol-1-yl)phenyl]methyl]-3-methyl-1H-indole-2-propanoic acid (1.0 g) in DMF (10 ml) is treated with SOCl2 (0.5 g) and, after cooling a gaseous NH3 is passed through the reaction mixture for 6 hours. The ammonium salt is filtered off and ether is added to the solution. The so obtai... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1c[nH]cn1.c1ccc2[nH]ccc2c1 | HO- | CN(C)C=O | null | 6 | Cc1c(CCC(=O)O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12.N>CN(C)C=O>Cc1c(CCC(N)=O)n(Cc2ccc(-n3ccnc3)cc2)c2ccc(F)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-19ddf36048d248e6b3036838b58d5b45 | C=C1CC(C(=O)OCC)C1.O>>C=C1CC(CO)C1CO | C(C)OC(=O)C1CC(C1)=C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)OCC.O.[OH-].[Na+].O>>OCC1C(C(C1)=C)CO | C[CH2:8]O[C:5]([CH:4]1[CH2:3][C:2](=[CH2:1])[CH2:7]1)=[O:6].[OH2:9]>>[CH2:1]=[C:2]1[CH2:3][CH:4]([CH2:5][OH:6])[CH:7]1[CH2:8][OH:9] | C=C1CC(C(=O)OCC)C1.O | C=C1CC(CO)C1CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ab614ca32202f1d8ea11d5cd45bbd2183fd62ba37e43955bce49c456e07489 | 71db72d5084a54806cd7dee46ed363229f26485e20995fa0990c12682ebbe8d8 | C=C1CCC1 | C-[CH2;D2;+0:1]-O-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]1-[C:5]-[C:6](=[C;D1;H2:7])-[CH2;D2;+0:8]-1.[OH2;D0;+0:9]>>[C;D1;H2:7]=[C:6]1-[C:5]-[C:4](-[CH2;D2;+0:2]-[OH;D1;+0:3])-[CH;D3;+0:8]-1-[CH2;D2;+0:1]-[OH;D1;+0:9] | 71 | [{"value": 71.0, "product": "OCC1C(C(C1)=C)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirred solution of 40.0 g (0.188 mol) of 1,2-bis(ethoxycarbonyl-3-methylenecyclobutane (Cripps, H. N.; Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 2723-2728) in 1.4 L of diethyl ether at 0° C. was added 14.4 g (0.379 mol) of lithium aluminum hydride in small portions. After 2 h at 0° C., 14.4 mL o... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Primary alcohol | C1CCC1 | C1CCC1 | C1CCC1 | HO- | null | null | 2 | C=C1CC(C(=O)OCC)C1.O>>C=C1CC(CO)C1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c0218d5b5bfa40d88a5132d0538e4b9e | C=C1CC(C(=O)O)C1.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>C=C1CC(N)(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C=C1CC(C1)C(=O)O.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(=O)C1(CC(C1)=C)N | O[C:6]([CH:4]1[CH2:3][C:2](=[CH2:1])[CH2:16]1)=[O:7].[OH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[N-]=[N+]=[N:5]P(=O)(c1ccccc1)c1ccccc1>>[CH2:1]=[C:2]1[CH2:3][C:4]([NH2:5])([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1 | C=C1CC(C(=O)O)C1.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | C=C1CC(N)(C(=O)OCc2ccccc2)C1 | null | null | C1(=CC=CC=C1)C.CCOCC | Protection | OtherReaction | 1184bfca77f96e369bf0d70b634df1b15f79fe759a1ad3575ddfc23f46ce1661 | 6f0d1f6478d58ca16a73cd9080147ce23383ab52e9ea815d30115a097e363852 | C=C1CC(C(=O)OCc2ccccc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[C:5](=[C;D1;H2:6])-[C:7]-1.O=P(-[N;H0;D2;+0:8]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[OH;D1;+0:9]-[C:10]-[c:11]>>[C;D1;H2:6]=[C:5]1-[C:4]-[C;H0;D4;+0:3](-[NH2;D1;+0:8])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:10]-[c:11])-[C:7]-1 | 68.5 | [{"value": 63.0, "product": "C(C1=CC=CC=C1)OC(=O)C1(CC(C1)=C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "C(C1=CC=CC=C1)OC(=O)C1(CC(C1)=C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | To a stirred solution of 26.7 g (238 mmol) of 3-methylenecyclobutane carboxylic acid (Cripps, H. N.; Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 2723-2728) in 100 mL of toluene at 0° C. was added 36.4 mL (262 mmol) of triethylamine and then 72.1 g (262 mmol) of diphenylphosphoryl azide. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Primary alcohol | Ester.Primary amine | C1CCC1.c1ccccc1.c1ccccc1 | C1CCC1 | C1CCC1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.CCOCC | 80 | 1 | C=C1CC(C(=O)O)C1.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C.CCOCC>C=C1CC(N)(C(=O)OCc2ccccc2)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-24eebc7913134719814d09f4259c412d | C=C1CC(CNC(=O)OC(C)(C)C)C1.CO>>CC(C)(C)OC(=O)NCC1CC(=O)C1 | C(C)(C)(C)OC(=O)NCC1CC(C1)=C.CO>>C(C)(C)(C)OC(=O)NCC1CC(C1)=O | C=[C:12]1[CH2:11][CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:14]1.C[OH:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][C:12](=[O:13])[CH2:14]1 | C=C1CC(CNC(=O)OC(C)(C)C)C1.CO | CC(C)(C)OC(=O)NCC1CC(=O)C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | ce24bdf7b8557608b45c098039b9dff56b7622168a77e980d5477497e4e9cec3 | b3f3e066e03c3af32b607e16083a7c1c9ca6bb82423de27d41bf12513c20f16d | O=C1CCC1 | C-[OH;D1;+0:1].C=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1 | null | [] | -78 | CELSIUS | 1 | HOUR | In a round bottom flask were placed 9 g of the product from Step A of Example 9, 100 mL of methanol, and 400 mL of dichloromethane. The solution was cooled to -78° C., and ozone was bubbled through the reaction mixture until the solution was blue. The system was flushed with nitrogen for 2.5 h, and then treated with 34... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Methanol | Ketone | C1CCC1 | C1CCC1 | C1CCC1 | Other | ClCCl | -78 | 1 | C=C1CC(CNC(=O)OC(C)(C)C)C1.CO>ClCCl>CC(C)(C)OC(=O)NCC1CC(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7ec30e53b2a04dcaad75f537b4457fc2 | CC(C)(C)[Si](C)(C)OC[C@H]1[C@H](CO[Si](C)(C)C(C)(C)C)C12CO2>>CC(C)(C)[Si](C)(C)OC[C@@H]1CC(=O)[C@H]1CO[Si](C)(C)C(C)(C)C | CC(C)(C)[Si](OC[C@@H]1C2(CO2)[C@H]1CO[Si](C)(C)C(C)(C)C)(C)C.[I-].[Li+]>>CC(C)(C)[Si](OC[C@@H]1C(C[C@H]1CO[Si](C)(C)C(C)(C)C)=O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C@@H:10]1[C:11]2([CH2:12][O:13]2)[C@H:14]1[CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C@@H:10]1[CH2:11][C:12](=[O:13])[C@H:14]1[CH2:15][O:16][Si:17]([CH3... | CC(C)(C)[Si](C)(C)OC[C@H]1[C@H](CO[Si](C)(C)C(C)(C)C)C12CO2 | CC(C)(C)[Si](C)(C)OC[C@@H]1CC(=O)[C@H]1CO[Si](C)(C)C(C)(C)C | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 88519533ad49dbbbfbe2d9b837d4428116548f4468cea37a430d5e5c760230ea | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCC1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[C@H;D3;+0:4](-[C:5]-[#8:6])-[C;H0;D4;+0:7]-12-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-2>>[#8:1]-[C:2]-[C@@H;D3;+0:3]1-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[CH2;D2;+0:7]-[C@H;D3;+0:4]-1-[C:5]-[#8:6] | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of 12.752 g (35.6 mmol) of [4R,5R]-4,5-bis(((1,1-dimethylethyl)-dimethylsilyl)oxymethyl)-1-oxaspiro[2,2]pentane, from Step D, in 50 mL of methylene chloride was added to a solution of 3.814 g (28.5 mmol) of lithium iodide in 200 mL of methylene chloride which had been cooled in an ice bath. After stirring th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1CC12CO2 | C1CCC1 | C1CCC1 | null | C(Cl)Cl | 0 | 1 | CC(C)(C)[Si](C)(C)OC[C@H]1[C@H](CO[Si](C)(C)C(C)(C)C)C12CO2>C(Cl)Cl>CC(C)(C)[Si](C)(C)OC[C@@H]1CC(=O)[C@H]1CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d480d233dea742e5bf153c3b7f49c34c | CC(C)(C)[Si](C)(C)OC[C@@H]1CC(=O)[C@H]1CO[Si](C)(C)C(C)(C)C.CON>>CON=C1C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C | CC(C)(C)[Si](OC[C@@H]1C(C[C@H]1CO[Si](C)(C)C(C)(C)C)=O)(C)C.Cl.O(C)N>>CON=C1[C@@H]([C@@H](C1)CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C | O=[C:4]1[CH2:5][C@@H:6]([CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[C@@H:16]1[CH2:17][O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25].[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3]=[C:4]1[CH2:5][C@@H:6]([CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[C@... | CC(C)(C)[Si](C)(C)OC[C@@H]1CC(=O)[C@H]1CO[Si](C)(C)C(C)(C)C.CON | CON=C1C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 6d7bccb4d1396d734317ff243e77bc67958c1f7ecfd535725774c12d212972a6 | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C1CCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1-[C:5].[C;D1;H3:6]-[#8:7]-[NH2;D1;+0:8]>>[C:5]-[C:4]1-[C:3]-[C:2]-[C;H0;D3;+0:1]-1=[N;H0;D2;+0:8]-[#8:7]-[C;D1;H3:6] | 75.7 | [{"value": 75.7, "product": "CON=C1[C@@H]([C@@H](C1)CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "CON=C1[C@@H]([C@@H](C1)CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 70 | MINUTE | A solution of 12.317 g (34.9 mmol) of [2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanone, from Step E, in 20 mL of pyridine was added to a solution of 3.160 g (37.8 mmol) of methoxylamine hydrochloride in 80 mL of pyridine. After stirring the reaction mixture for 70 min at ambient temperature, it... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | C1CCC1 | C1CCC1 | C1CCC1 | HO- | N1=CC=CC=C1 | null | 1.166667 | CC(C)(C)[Si](C)(C)OC[C@@H]1CC(=O)[C@H]1CO[Si](C)(C)C(C)(C)C.CON>N1=CC=CC=C1>CON=C1C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9dab2a8813514c6ebc5f9dee4fe82a4c | CON=C1C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C>>CC(C)(C)[Si](C)(C)OC[C@@H]1C[C@@H](N)[C@@H]1CO[Si](C)(C)C(C)(C)C | CON=C1[C@@H]([C@@H](C1)CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C.[BH4-].[Na+].FC(C(=O)O)(F)F>>CC(C)(C)[Si](OC[C@H]1[C@@H](C[C@H]1CO[Si](C)(C)C(C)(C)C)N)(C)C | CO[N:13]=[C:12]1[CH2:11][C@@H:10]([CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[C@H:14]1[CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C@@H:10]1[CH2:11][C@@H:12]([NH2:13])[C@@H:14]1[CH2:15][O:16][Si:17... | CON=C1C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C | CC(C)(C)[Si](C)(C)OC[C@@H]1C[C@@H](N)[C@@H]1CO[Si](C)(C)C(C)(C)C | null | null | O1CCCC1 | Reduction | OtherReaction | f62bd5fff0d17c24f6888b87f30e074b2c0c966ea5cb55957cdb2d1bb69926f0 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | C1CCC1 | C-O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1-[C:6]>>[C:6]-[C:5]1-[C:4]-[C:3]-[C@H;D3;+0:2]-1-[NH2;D1;+0:1] | 115.6 | [{"value": 115.6, "product": "CC(C)(C)[Si](OC[C@H]1[C@@H](C[C@H]1CO[Si](C)(C)C(C)(C)C)N)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To 4.74 g (125 mmol) of sodium borohydride in 125 mL of tetrahydrofuran (THF) was added (slowly) 14.25 g (9.63 mL, 125 mmol) of trifluoroacetic acid (TFA), followed by 10.228 g (26.4 mmol) of [2R,3R]-2,3-Bis(((1,1-dimethylethyl)di-methylsilyl)oxymethyl)cyclobutanone-O-methyl oxime, from Step F, in 25 mL of THF. After s... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | C1CCC1 | C1CCC1 | C1CCC1 | Other | O1CCCC1 | null | 1.5 | CON=C1C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C>O1CCCC1>CC(C)(C)[Si](C)(C)OC[C@@H]1C[C@@H](N)[C@@H]1CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-75cc9b295ae2417ba2904b5a087cdddf | COC(=O)C1=CCC1.Nc1ncnc2nc[nH]c12>>COC(=O)C1CCC1n1cnc2c(N)ncnc21 | C1CCC2=NCCCN2CC1.N1=CN=C2N=CNC2=C1N.C1(=CCC1)C(=O)OC.C1CCC2=NCCCN2CC1>>COC(=O)C1C(CC1)N1C2=NC=NC(=C2N=C1)N | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[CH:8][CH2:7][CH2:6]1.[n:9]1[cH:10][nH:11][c:12]2[c:13]([NH2:14])[n:15][cH:16][n:17][c:18]12>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]1[n:9]1[cH:10][n:11][c:12]2[c:13]([NH2:14])[n:15][cH:16][n:17][c:18]12 | COC(=O)C1=CCC1.Nc1ncnc2nc[nH]c12 | COC(=O)C1CCC1n1cnc2c(N)ncnc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 0dce6c9da6571ae879fef58e5b71ad9d1bdd8daa2082281dabfaf3c7305b67d9 | 86272a5f6ad2cca86dc8534964509c004e69b8eed92d84449655390f898d542d | c1ncc2ncn(C3CCC3)c2n1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5]1=[CH;D2;+0:6]-[C:7]-[C:8]-1.[N;D1;H2:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]2:[n;H0;D2;+0:15]:[c:16]:[nH;D2;+0:17]:[c:18]:1:2>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[C:8]-[C:7]-[CH;D3;+0:6]-1-[n;H0;D3;+0:15]1:[c:16]:[n;H0;D2;+0:17]:[c:18]2:[c:10]... | 61 | [{"value": 61.0, "product": "COC(=O)C1C(CC1)N1C2=NC=NC(=C2N=C1)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 66 | HOUR | Adenine (486 mg, 3.6 mmol) was combined with an excess of methyl 1-cyclobutene carboxylate (~25 mmol) from Step B of Example 35 and 53 μL (0.36 mmol) of DBU in 75 mL of acetonitrile and the mixture was stirred at ambient temperature, under a nitrogen atmosphere. After 66 h, a second 53 μL aliquot of DBU was added and s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1=CCC1.c1ncc2nc[nH]c2n1 | C1CCC1.c1ncnc2[nH]cnc12 | C1CCC1.c1ncnc2[nH]cnc12 | null | C(C)#N | null | 66 | COC(=O)C1=CCC1.Nc1ncnc2nc[nH]c12>C(C)#N>COC(=O)C1CCC1n1cnc2c(N)ncnc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-048b5067c6284c43800165c2eb0e4b52 | COC(=O)C1CCC1n1cnc2c(N)ncnc21>>Nc1ncnc2c1ncn2C1CCC1CO | COC(=O)C1C(CC1)N1C2=NC=NC(=C2N=C1)N.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OCC1C(CC1)N1C2=NC=NC(=C2N=C1)N | CO[C:15]([CH:14]1[CH:11]([n:10]2[c:6]3[n:5][cH:4][n:3][c:2]([NH2:1])[c:7]3[n:8][cH:9]2)[CH2:12][CH2:13]1)=[O:16]>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[CH:11]1[CH2:12][CH2:13][CH:14]1[CH2:15][OH:16] | COC(=O)C1CCC1n1cnc2c(N)ncnc21 | Nc1ncnc2c1ncn2C1CCC1CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ncc2ncn(C3CCC3)c2n1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | 97.1 | [{"value": 97.0, "product": "OCC1C(CC1)N1C2=NC=NC(=C2N=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "OCC1C(CC1)N1C2=NC=NC(=C2N=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 9-(2-methoxycarbonyl-1-cyclobutyl)adenine (500 mg, 2.02 mmol) from Step A was dissolved in 250 mL of THF and the solution was cooled to 0° C. with stirring under a nitrogen atmosphere. Lithium aluminum hydride (115 mg, 3.03 mmol) was added and the reaction mixture was stirred for 30 minutes then quenched with 115 μL of... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ncnc2nc[nH]c12.C1CCC1 | Other | C1CCOC1 | 0 | null | COC(=O)C1CCC1n1cnc2c(N)ncnc21>C1CCOC1>Nc1ncnc2c1ncn2C1CCC1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-24435b4afdfa4eebb5264d51b0d621a6 | Nc1ncnc2c1ncn2C1CC(CO)C1CO>>CC1CC(n2cnc3c(N)ncnc32)C1CO | OCC1C(CC1CO)N1C=2N=C(NC(C2N=C1)=O)N.OCC1C(CC1CO)N1C2=NC=NC(=C2N=C1)N>>OCC1C(CC1C)N1C2=NC=NC(=C2N=C1)N | O[CH2:1][CH:2]1[CH2:3][CH:4]([n:5]2[cH:6][n:7][c:8]3[c:9]([NH2:10])[n:11][cH:12][n:13][c:14]23)[CH:15]1[CH2:16][OH:17]>>[CH3:1][CH:2]1[CH2:3][CH:4]([n:5]2[cH:6][n:7][c:8]3[c:9]([NH2:10])[n:11][cH:12][n:13][c:14]23)[CH:15]1[CH2:16][OH:17] | Nc1ncnc2c1ncn2C1CC(CO)C1CO | CC1CC(n2cnc3c(N)ncnc32)C1CO | null | null | null | Reduction | OtherReaction | 1deafbccd34c1d747dea179c0b63e48cd7fc76936d377fecabe099ecef578991 | 0a2c8330040d049ae67653e1474aff520bf8a2d8c908ffd7076f536576936945 | c1ncc2ncn(C3CCC3)c2n1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[CH3;D1;+0:1])-[C:4] | null | [] | null | null | null | null | Following the procedures described in Example 40, replacing 9-(2',3'-bis(hydroxymethyl)-cyclobutyl)guanine, the product of Example 1, with 9-(2',3'-bis(hydroxymethyl)cyclobutyl)adenine, Example 4, the title compound is prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | C1CCC1.c1ncnc2[nH]cnc12 | Other | null | null | null | Nc1ncnc2c1ncn2C1CC(CO)C1CO>>CC1CC(n2cnc3c(N)ncnc32)C1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a85057aaa6914c52a223e4b75364a097 | CC(C)(C)[Si](C)(C)OCC1CC(=O)C1CO[Si](C)(C)C(C)(C)C>>CC(C)(C)[Si](C)(C)OCC1CC(O)C1CO[Si](C)(C)C(C)(C)C | C(C)(=O)O.CCC([BH-](C(CC)C)C(CC)C)C.[K+].CC(C)(C)[Si](OCC1C(CC1CO[Si](C)(C)C(C)(C)C)=O)(C)C.C(C)(CC)[BH-](C(C)CC)C(C)CC.[K+]>>CC(C)(C)[Si](OCC1C(CC1CO[Si](C)(C)C(C)(C)C)O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH:10]1[CH2:11][C:12](=[O:13])[CH:14]1[CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH:10]1[CH2:11][CH:12]([OH:13])[CH:14]1[CH2:15][O:16][Si:17]([CH3:18])(... | CC(C)(C)[Si](C)(C)OCC1CC(=O)C1CO[Si](C)(C)C(C)(C)C | CC(C)(C)[Si](C)(C)OCC1CC(O)C1CO[Si](C)(C)C(C)(C)C | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | a4850c27489f585e297ba8e69ff2fc4a78564778d9ebc64c3ad812298c588873 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1CCC1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5]-1=[O;H0;D1;+0:6]>>[C:1]-[C:2]1-[C:3]-[C:4]-[CH;D3;+0:5]-1-[OH;D1;+0:6] | 62 | [{"value": 62.0, "product": "CC(C)(C)[Si](OCC1C(CC1CO[Si](C)(C)C(C)(C)C)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.5, "product": "CC(C)(C)[Si](OCC1C(CC1CO[Si](C)(C)C(C)(C)C)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanone (10.2 g, 28.4 mmol) from Step B was dissolved in tetrahydrofuran (THF) and the solution was cooled to -78° C. under a nitrogen atmosphere. To the THF solution at -78° C. was slowly added, with stirring, 31 mL (31 mmol) of potassium tri-sec-butylborohydri... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCC1 | C1CCC1 | C1CCC1 | null | O1CCCC1 | -78 | null | CC(C)(C)[Si](C)(C)OCC1CC(=O)C1CO[Si](C)(C)C(C)(C)C>O1CCCC1>CC(C)(C)[Si](C)(C)OCC1CC(O)C1CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a3501c466ca1436bb389403a5114d62c | CC(C)(C)[Si](C)(C)OCC1CC(O)C1CO[Si](C)(C)C(C)(C)C>>OCC1CC(O)C1CO | CC(C)(C)[Si](OCC1C(CC1CO[Si](C)(C)C(C)(C)C)O)(C)C.Cl[Si](C)(C)C>>OCC1C(CC1CO)O | CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH:3]1[CH2:4][CH:5]([OH:6])[CH:7]1[CH2:8][O:9][Si](C)(C)C(C)(C)C>>[OH:1][CH2:2][CH:3]1[CH2:4][CH:5]([OH:6])[CH:7]1[CH2:8][OH:9] | CC(C)(C)[Si](C)(C)OCC1CC(O)C1CO[Si](C)(C)C(C)(C)C | OCC1CC(O)C1CO | null | null | CO | Deprotection | OtherReaction | 1619c5ee9c412d78d58da0e1c017876e5d0cace6a46e5e8606a374402a7e53de | a8805f3806094760f99d243d0b2d2636a5b3ac8fc7951b6f30153f62002828e0 | C1CCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5]-[O;H0;D2;+0:6]-[Si](-C)(-C)-C(-C)(-C)-C>>[OH;D1;+0:1]-[C:2]-[C:3]-[C:4]-[C:5]-[OH;D1;+0:6] | null | [] | null | null | 0.5 | HOUR | 2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanol (6.3 g, 17.5 mmol) from Step C was combined with 5.3 mL (43 mmol) of chlorotrimethyl-silane in 103 mL of methanol. The reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 0.5 h then concentrated under reduced pressure to an... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Primary alcohol.Primary alcohol | null | null | C1CCC1 | Other | CO | null | 0.5 | CC(C)(C)[Si](C)(C)OCC1CC(O)C1CO[Si](C)(C)C(C)(C)C>CO>OCC1CC(O)C1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3d62ca5f75db401fa27c51497eb470a9 | O=C(OC1CC(CO)C1CBr)c1ccccc1>>C=C1C(CO)CC1OC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)CBr.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1CCOC1>>C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=C | Br[CH2:1][CH:2]1[CH:3]([CH2:4][OH:5])[CH2:6][CH:7]1[O:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH2:1]=[C:2]1[CH:3]([CH2:4][OH:5])[CH2:6][CH:7]1[O:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=C(OC1CC(CO)C1CBr)c1ccccc1 | C=C1C(CO)CC1OC(=O)c1ccccc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 0794b0188fe495178ef67f4d49d6c20c1ce3a37677bf294953c9681b3103be04 | 390fd58f5ee2898074a21589b1498013a0dd9c1d8d67db11ba35b62c01461363 | C=C1CCC1OC(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[C:3](-[C:4])-[C:5]-[C:6]-1-[#8:7]-[C:8]=[O;D1;H0:9]>>[C:4]-[C:3]1-[C:5]-[C:6](-[#8:7]-[C:8]=[O;D1;H0:9])-[C;H0;D3;+0:2]-1=[CH2;D1;+0:1] | 85 | [{"value": 85.0, "product": "C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1-Benzoyloxy-2-bromomethyl-3-hydroxymethylcyclobutane (2.5 g, 8.36 mmol) from Step F and tetra-n-butylammonium fluoride ((8.1 g, 25 mmol) were combined in 200 mL of freshly distilled THF and the reaction mixture was stirred at ambient temperature, under a nitrogen atmosphere, overnight. The volume of the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Vinyl | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1 | HBr | C(Cl)Cl | null | 8 | O=C(OC1CC(CO)C1CBr)c1ccccc1>C(Cl)Cl>C=C1C(CO)CC1OC(=O)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-399011f1b64c4ac8aa1d59f797b46087 | C=C1C(CO)CC1OC(=O)c1ccccc1.CO>>O=C(OC1CC(CO)C1=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=C.C(Cl)Cl.CO>>C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=O | C=[C:9]1[CH:4]([O:3][C:2](=[O:1])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:5][CH:6]1[CH2:7][OH:8].C[OH:10]>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][CH:6]([CH2:7][OH:8])[C:9]1=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C=C1C(CO)CC1OC(=O)c1ccccc1.CO | O=C(OC1CC(CO)C1=O)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ce24bdf7b8557608b45c098039b9dff56b7622168a77e980d5477497e4e9cec3 | b3f3e066e03c3af32b607e16083a7c1c9ca6bb82423de27d41bf12513c20f16d | O=C(OC1CCC1=O)c1ccccc1 | C-[OH;D1;+0:1].C=[C;H0;D3;+0:2]1-[C:3](-[#8:4]-[C:5]=[O;D1;H0:6])-[C:7]-[C:8]-1-[C:9]>>[C:9]-[C:8]1-[C:7]-[C:3](-[#8:4]-[C:5]=[O;D1;H0:6])-[C;H0;D3;+0:2]-1=[O;H0;D1;+0:1] | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | A mixture of 2.09 g (9.5 mmol) of 1-benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane from Step G, 112 mL of methylene chloride and 28 mL of methanol was cooled to -78° C. under a nitrogen atmosphere. Ozone was bubbled through the mixture for 10 minutes, until a persistent blue color was observed. Excess ozone was flus... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Methanol | Ketone | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1 | Other | null | -78 | 0.5 | C=C1C(CO)CC1OC(=O)c1ccccc1.CO>>O=C(OC1CC(CO)C1=O)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c6befcbde27c4bafadace118dde28422 | O=C(OC1CC(CO)C1=O)c1ccccc1>>O=C(OC1CC(CO)C1O)c1ccccc1 | [BH4-].[Na+].C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)=O.[BH4-]>>C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)O | [O:1]=[C:2]([O:3][CH:4]1[CH2:5][CH:6]([CH2:7][OH:8])[C:9]1=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][CH:6]([CH2:7][OH:8])[CH:9]1[OH:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=C(OC1CC(CO)C1=O)c1ccccc1 | O=C(OC1CC(CO)C1O)c1ccccc1 | null | null | C(C)(=O)O | Reduction | Reduction of ketone to secondary alcohol | a4850c27489f585e297ba8e69ff2fc4a78564778d9ebc64c3ad812298c588873 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(OC1CCC1)c1ccccc1 | [C:1]-[C:2]1-[C:3]-[C:4](-[#8:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[C:2]1-[C:3]-[C:4](-[#8:5]-[C:6]=[O;D1;H0:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 101.8 | [{"value": 101.8, "product": "C(C1=CC=CC=C1)(=O)OC1C(C(C1)CO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Glacial acetic acid in (25 mL) a 250 mL 3-neck flask was cooled in an ice bath under a stream of nitrogen. Sodium borohydride was added cautiously in portions over a 5 minute period. The ice bath removed and the reagent was used after stirring for 15 minutes at ambient temperature. 2-Benzoyloxy-4-hydroxymethylcyclobuta... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1 | null | C(C)(=O)O | null | 0.25 | O=C(OC1CC(CO)C1=O)c1ccccc1>C(C)(=O)O>O=C(OC1CC(CO)C1O)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2552c2be6a3476ba74b5072c8d48404 | CC(C)(C)[Si](OCC1CC(O)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1.CS(=O)(=O)Cl>>CC(C)(C)[Si](OCC1CC(OS(C)(=O)=O)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 | CS(=O)(=O)Cl.CC(C)(C)[Si](OC1C(CC1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>>CS(=O)(=O)OC1C(C(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][CH:8]1[CH2:9][CH:10]([OH:11])[CH:16]1[O:17][Si:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[C:31]([CH3:32])([CH3:33])[CH3:34])([c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1)[c:41]1[cH:42][cH:43][cH:44][cH:45][cH:46]1.Cl[S:1... | CC(C)(C)[Si](OCC1CC(O)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1.CS(=O)(=O)Cl | CC(C)(C)[Si](OCC1CC(OS(C)(=O)=O)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | c1ccc([SiH](OCC2CCC2O[SiH](c2ccccc2)c2ccccc2)c2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8] | 60 | [{"value": 60.0, "product": "CS(=O)(=O)OC1C(C(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "CS(=O)(=O)OC1C(C(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C", "details... | null | null | 3.5 | HOUR | Freshly distilled triethylamine (1.28 g, 8.2 mmol) was dissolved in 75 mL of freshly distilled methylene chloride. To this solution was added 2.3 g (3.9 mmol) of 2-O-((1,1-dimethylethyl)diphenylsilyl)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1,2-cyclobutanediol from Step K and the resultant solution was cooled... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CCC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 3.5 | CC(C)(C)[Si](OCC1CC(O)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)[Si](OCC1CC(OS(C)(=O)=O)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d7295c19f6b346c7b7c965bccf92eca4 | CC(C)(C)[Si](OCC1CC(N=[N+]=[N-])(O[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)C1)(c1ccccc1)c1ccccc1>>CC(C)(C)[Si](OCC1CC(N)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 | CC(C)(C)[Si](OC1(CC(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)N=[N+]=[N-])(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)[O-].[NH4+]>>CC(C)(C)[Si](OC1C(CC1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)N)(C1=CC=CC=C1)C1=CC=CC=C1 | [N-]=[N+]=[N:11][C:10]1([O:13][Si:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:9][CH:8]([CH2:7][O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[CH2:... | CC(C)(C)[Si](OCC1CC(N=[N+]=[N-])(O[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)C1)(c1ccccc1)c1ccccc1 | CC(C)(C)[Si](OCC1CC(N)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 | null | [Pd] | CO | Miscellaneous | OtherReaction | f6f6d83f16f09b33edb1f9ef3261d63e6b0f23dc94a62b436f853e983ec9d730 | f4d87f28c9e9f705e45827638f0c1b5f77e69c390fd5caed40f3fbb1d17086a5 | c1ccc([SiH](OCC2CCC2O[SiH](c2ccccc2)c2ccccc2)c2ccccc2)cc1 | [C:1]-[#14:2](-[c:3])(-[c:4])-[O;H0;D2;+0:5]-[C;H0;D4;+0:6]1(-[N;H0;D2;+0:7]=[N+]=[N-])-[C:8]-[C:9](-[C:10])-[CH2;D2;+0:11]-1>>[C:1]-[#14:2](-[c:3])(-[c:4])-[O;H0;D2;+0:5]-[CH;D3;+0:11]1-[C:9](-[C:10])-[C:8]-[CH;D3;+0:6]-1-[NH2;D1;+0:7] | 184.5 | [{"value": 92.0, "product": "CC(C)(C)[Si](OC1C(CC1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)N)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 184.5, "product": "CC(C)(C)[Si](OC1C(CC1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)N)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYI... | null | null | 23 | HOUR | 2-(((1,1-dimethylethyl)diphenylsilyloxy)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1-azidocyclobutane (800 mg, 1.29 mmol), the product of Step M, was dissolved in 20 mL of methanol. To this solution was added 200 mg of 5% palladium on carbon, followed by 420 mg of ammonium formate. The flask was stoppered and th... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].CO | null | 23 | CC(C)(C)[Si](OCC1CC(N=[N+]=[N-])(O[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)C1)(c1ccccc1)c1ccccc1>[Pd].CO>CC(C)(C)[Si](OCC1CC(N)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-49aff4ea23944bc0a96ad4f0565e2869 | CC(C)(C)[Si](OCC1CC(N)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1.Nc1nc(O)c([N+](=O)[O-])c(Cl)n1>>CC(C)(C)[Si](OCC1CC(Nc2nc(N)nc(O)c2[N+](=O)[O-])C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 | C(C)N(CC)CC.CC(C)(C)[Si](OC1C(CC1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)N)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)(C)[Si](OC1C(CC1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)N)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC.NC1=NC(=C(C(=N1)O)[N+](=O)[O-])Cl>>NC1=NC(=C(C(=N1)O)[N+](=O)[O-])NC1C(C(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O[Si]... | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][CH:8]1[CH2:9][CH:10]([NH2:11])[CH:23]1[O:24][Si:25]([c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)([c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[C:38]([CH3:39])([CH3:40])[CH3:41])([c:42]1[cH:43][cH:44][cH:45][cH:46][cH:47]1)[c:48]1[cH:49][cH:50][cH:51][cH:52][cH:53]1.Cl[c:... | CC(C)(C)[Si](OCC1CC(N)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1.Nc1nc(O)c([N+](=O)[O-])c(Cl)n1 | CC(C)(C)[Si](OCC1CC(Nc2nc(N)nc(O)c2[N+](=O)[O-])C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([SiH](OCC2CC(Nc3ccncn3)C2O[SiH](c2ccccc2)c2ccccc2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[O;D1;H1:6]):[c:7]:1-[#7;+:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[#7;+:8]-[c:7]1:[c:5](-[O;D1;H1:6]):[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12] | 64 | [{"value": 64.0, "product": "NC1=NC(=C(C(=N1)O)[N+](=O)[O-])NC1C(C(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.9, "product": "NC1=NC(=C(C(=N1)O)[N+](=O)[O-])NC1C(C(C1)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O[Si](C1... | 50 | CELSIUS | 2.5 | HOUR | 2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1-aminocyclobutane (588 mg, 0.99 mmol), the product of Step N, 189 mg (0.99 mmol) of 2-amino-6-chloro-4-hydroxy-5-nitropyrimidine (prepared as described by J. F. Constant, et al. in J. Heterocyclic Chem, 1035 (1985)) and triethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CCC1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | 50 | 2.5 | CC(C)(C)[Si](OCC1CC(N)C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1.Nc1nc(O)c([N+](=O)[O-])c(Cl)n1>CN(C)C=O>CC(C)(C)[Si](OCC1CC(Nc2nc(N)nc(O)c2[N+](=O)[O-])C1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-498232fddde34261911c12c5c23147f0 | COC1(OC)CC(C(=O)OC(C)C)(C(=O)OC(C)C)C1>>COC1(OC)CC(CO)(CO)C1 | COC1(CC(C1)(C(=O)OC(C)C)C(=O)OC(C)C)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OCC1(CC(C1)(OC)OC)CO | CC(C)O[C:8]([C:7]1([C:10](OC(C)C)=[O:11])[CH2:6][C:3]([O:2][CH3:1])([O:4][CH3:5])[CH2:12]1)=[O:9]>>[CH3:1][O:2][C:3]1([O:4][CH3:5])[CH2:6][C:7]([CH2:8][OH:9])([CH2:10][OH:11])[CH2:12]1 | COC1(OC)CC(C(=O)OC(C)C)(C(=O)OC(C)C)C1 | COC1(OC)CC(CO)(CO)C1 | null | null | CCOCC.C(C)OCC | Reduction | OtherReaction | 8eb0b0948ba02d6bff2e6dcc47886480a262869f201923801796429d5f921f16 | 3906c52a610c5241bd14656b0a46d01a4c70864c3b16d9b6e34a49708e61df8d | C1CCC1 | C-C(-C)-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C(-C)-C)(-[C:6])-[C:7]>>[C:6]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])(-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:7] | 41.2 | [{"value": 41.0, "product": "OCC1(CC(C1)(OC)OC)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.2, "product": "OCC1(CC(C1)(OC)OC)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Diisopropyl 3,3-dimethoxy-cyclobutane-1,1-dicarboxylate (6.0 g, 20.8 mmol), prepared as described by P. E. Pigou and C. H. Schiesser, J Org Chem, 53, 3841-3 (1988), was dissolved in 200 mL of anhydrous diethyl ether and the ether solution was cooled to 0° C. with stirring under a nitrogen atmosphere. Lithium aluminum h... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol.Primary alcohol | null | null | C1CCC1 | HO- | CCOCC.C(C)OCC | null | null | COC1(OC)CC(C(=O)OC(C)C)(C(=O)OC(C)C)C1>CCOCC.C(C)OCC>COC1(OC)CC(CO)(CO)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-df3e718428eb4b82b1a1f65e66c2e7ef | CC(C)(C)[Si](C)(C)Cl.COC1(OC)CC(CO)(CO)C1.CON>>CON=C1CC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)C1 | Cl.O(C)N.[Si](C)(C)(C(C)(C)C)Cl.OCC1(CC(C1)(OC)OC)CO.Cl.[OH-]>>CON=C1CC(C1)(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C | Cl[Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:21])[CH3:24].O([C:4]1(O[CH3:19])[CH2:5][C:6]([CH2:7][OH:8])([CH2:14][OH:17])[CH2:25]1)[CH3:15].[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3]=[C:4]1[CH2:5][C:6]([CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])([CH2:16][O:17][Si:18]([CH3:19])([CH3:20])[C... | CC(C)(C)[Si](C)(C)Cl.COC1(OC)CC(CO)(CO)C1.CON | CON=C1CC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)C1 | null | null | C1CCOC1.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | af38517e993aff00770f29393680d457657c2a9d3da8f034212a31bca1ea7691 | 3fe8ba001752dbf53ed1efd94db8f178a383ef497815de4dc8a42a45c96f80af | N=C1CCC1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[CH3;D1;+0:6])-[CH3;D1;+0:7].[C;D1;H3:8]-[#8:9]-[NH2;D1;+0:10].[CH3;D1;+0:11]-O-[C;H0;D4;+0:12]1(-O-[CH3;D1;+0:13])-[C:14]-[C;H0;D4;+0:15](-[C:16]-[OH;D1;+0:17])(-[CH2;D2;+0:18]-[OH;D1;+0:19])-[C:20]-1>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3]... | 20 | [{"value": 20.0, "product": "CON=C1CC(C1)(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.7, "product": "CON=C1CC(C1)(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 3,3-Bis(hydroxymethyl)-1,1-dimethoxycyclobutane (1.35 g, 7.65 mmol) from Step A and 3.8 mL of 2M aqueous hydrochloric acid solution were added to 60 mL of THF and the reaction mixture was stirred at ambient temperature for 0.5 h, under a nitrogen atmosphere. The reaction mixture was neutralized by the addition of a str... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Primary alcohol.Primary amine.Silyl protective group | TMS ether protective group.TMS ether protective group | C1CCC1 | C1CCC1 | C1CCC1 | null | C1CCOC1.N1=CC=CC=C1 | null | 0.5 | CC(C)(C)[Si](C)(C)Cl.COC1(OC)CC(CO)(CO)C1.CON>C1CCOC1.N1=CC=CC=C1>CON=C1CC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-172fe4077e1e42b09cf936e4e5ad0591 | C=C1CC(NC(=O)OCc2ccccc2)C1.CO>>O=C1CC(NC(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)NC1CC(C1)=C.CO>>C(C1=CC=CC=C1)OC(=O)NC1CC(C1)=O | C=[C:2]1[CH2:3][CH:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1.C[OH:1]>>[O:1]=[C:2]1[CH2:3][CH:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1 | C=C1CC(NC(=O)OCc2ccccc2)C1.CO | O=C1CC(NC(=O)OCc2ccccc2)C1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | ce24bdf7b8557608b45c098039b9dff56b7622168a77e980d5477497e4e9cec3 | b3f3e066e03c3af32b607e16083a7c1c9ca6bb82423de27d41bf12513c20f16d | O=C1CC(NC(=O)OCc2ccccc2)C1 | C-[OH;D1;+0:1].C=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1 | 93 | [{"value": 93.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1CC(C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | N-(Benzyloxycarbonyl)-3-methylenecyclobutanamine (4 g, 18.4 mmol) from Step A of Example 5, 34 mL of methanol and 136 mL of methylene chloride were mixed together and cooled to -78° C. under a nitrogen atmosphere. Ozone was bubbled through the mixture for approximately 20 minutes and then the reaction mixture was flush... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Methanol | Ketone | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1 | Other | C(Cl)Cl | -78 | 0.5 | C=C1CC(NC(=O)OCc2ccccc2)C1.CO>C(Cl)Cl>O=C1CC(NC(=O)OCc2ccccc2)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fd6fdf93390a493cadbd207269966ea5 | O=C1CC(NC(=O)OCc2ccccc2)C1>>O=C(NC1CC(O)C1)OCc1ccccc1 | C(C)(=O)O.CCC([BH-](C(CC)C)C(CC)C)C.[K+].C(C1=CC=CC=C1)OC(=O)NC1CC(C1)=O.C(C)(CC)[BH-](C(C)CC)C(C)CC.[K+]>>C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O | [O:1]=[C:2]([NH:3][CH:4]1[CH2:5][C:6](=[O:7])[CH2:8]1)[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH:6]([OH:7])[CH2:8]1)[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=C1CC(NC(=O)OCc2ccccc2)C1 | O=C(NC1CC(O)C1)OCc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | a4850c27489f585e297ba8e69ff2fc4a78564778d9ebc64c3ad812298c588873 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(NC1CCC1)OCc1ccccc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[C:5]-1 | 63 | [{"value": 63.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone (3.51 g, 16.0 mmol) from Step A was dissolved in 100 mL of THF and the THF solution was cooled to -78° C. with stirring under a nitrogen atmosphere. To the solution was added 17.6 mL (17.6 mmol) of potassium tri-sec-butylborohydride (sold by Aldrich Chemical Company as a 1M... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1 | null | C1CCOC1 | 0 | 0.166667 | O=C1CC(NC(=O)OCc2ccccc2)C1>C1CCOC1>O=C(NC1CC(O)C1)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5c18cd13ada34da58bb93de0840a40a7 | CC(C)(C)[Si](C)(C)Cl.O=C(NC1CC(O)C1)OCc1ccccc1>>CC(C)(C)[Si](C)(C)OC1CC(NC(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O.[Si](C)(C)(C(C)(C)C)Cl>>C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O[Si](C)(C)C(C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH:9]1[CH2:10][CH:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:... | CC(C)(C)[Si](C)(C)Cl.O=C(NC1CC(O)C1)OCc1ccccc1 | CC(C)(C)[Si](C)(C)OC1CC(NC(=O)OCc2ccccc2)C1 | null | null | N1=CC=CC=C1 | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | O=C(NC1CCC1)OCc1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11] | 94.2 | [{"value": 88.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "C(C1=CC=CC=C1)OC(=O)NC1CC(C1)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 65 | HOUR | N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanol (2.22 g, 10 mmol) from Step B and t-butyldimethylsilyl chloride (4.8 g, 32 mmol) were combined in 25 mL of anhydrous pyridine and the cloudy suspension was stirred over the weekend at ambient temperature, under a nitrogen atmosphere. After 65 h, the solution was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | C1CCC1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 65 | CC(C)(C)[Si](C)(C)Cl.O=C(NC1CC(O)C1)OCc1ccccc1>N1=CC=CC=C1>CC(C)(C)[Si](C)(C)OC1CC(NC(=O)OCc2ccccc2)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0e97936974da410d9d6fe7fab4bd1b46 | CC(C)(C)[Si](C)(C)OCCC1C(O)CC1CO[Si](C)(C)C(C)(C)C.CS(=O)(=O)Cl>>CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1OS(C)(=O)=O | CS(=O)(=O)Cl.CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)O)(C)C.C(C)N(CC)CC>>CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)OS(=O)(=O)C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]1[CH:12]([CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH:23]1[OH:24].Cl[S:25]([CH3:26])(=[O:27])=[O:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]1[CH:12]([CH2... | CC(C)(C)[Si](C)(C)OCCC1C(O)CC1CO[Si](C)(C)C(C)(C)C.CS(=O)(=O)Cl | CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1OS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8] | 89 | [{"value": 89.0, "product": "CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)OS(=O)(=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 2-(2-((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)cyclobutanol (160 mg, 0.43 mmol) from Step B was dissolved in 2 mL of methylene chloride and the resultant solution was cooled to 0° C. Triethylamine (120μL) was added, followed by 36 μL of methanesulfonyl chloride. After ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CCC1 | HCl | C(Cl)Cl | 0 | 0.5 | CC(C)(C)[Si](C)(C)OCCC1C(O)CC1CO[Si](C)(C)C(C)(C)C.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1OS(C)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d5f0c7a4ccb444f19b70b9728ca3aa5e | CC(C)(C)[Si](C)(C)OCCC1(OS(C)(=O)=O)CC(CO[Si](C)(C)C(C)(C)C)C1.[N-]=[N+]=[N-]>>CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1N=[N+]=[N-] | CC(C)(C)[Si](OCCC1(CC(C1)CO[Si](C)(C)C(C)(C)C)OS(=O)(=O)C)(C)C.[N-]=[N+]=[N-].[Li+]>>CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-])(C)C | CS(=O)(=O)O[C:11]1([CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:22][CH:12]([CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:23]1.[N-:24]=[N+:25]=[N-:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]1[CH:12]([CH2:13][... | CC(C)(C)[Si](C)(C)OCCC1(OS(C)(=O)=O)CC(CO[Si](C)(C)C(C)(C)C)C1.[N-]=[N+]=[N-] | CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1N=[N+]=[N-] | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a3da497eb98edf86a6ac639488f229d11c4b40b14cd1b75141de5c7286b2bfb4 | 5f2cb2b9819a73a6855f5277f7fe9d5ce3871340baaebb59d42e38e1ca145c0a | C1CCC1 | C-S(=O)(=O)-O-[C;H0;D4;+0:1]1(-[C:2]-[C:3])-[CH2;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[#8:7])-[CH2;D2;+0:8]-1.[N-;H0;D1:9]=[#7;+:10]=[N;-;D1;H0:11]>>[#8:7]-[C:6]-[CH;D3;+0:5]1-[CH2;D2;+0:4]-[CH;D3;+0:8](-[N;H0;D2;+0:9]=[#7;+:10]=[N;-;D1;H0:11])-[CH;D3;+0:1]-1-[C:2]-[C:3] | 146.4 | [{"value": 73.0, "product": "CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-])(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 146.4, "product": "CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-])(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)-1-O-methanesulfonylcyclobutanol (180 mg, 0.41 mmol) was mixed with 200 mg (4.1 mmol) of lithium azide in 4 mL of DMF. The reaction mixture was heated at 80° C. for 2 h then concentrated in vacuo. The residue was purified ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Azide | C1CCC1 | C1CCC1 | C1CCC1 | MsOH.HO- | CN(C)C=O | 80 | null | CC(C)(C)[Si](C)(C)OCCC1(OS(C)(=O)=O)CC(CO[Si](C)(C)C(C)(C)C)C1.[N-]=[N+]=[N-]>CN(C)C=O>CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1N=[N+]=[N-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-93dc134eaa724c8da64367a390ea75ae | CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1N=[N+]=[N-]>>CC(C)(C)[Si](C)(C)OCCC1C(N)CC1CO[Si](C)(C)C(C)(C)C | CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-])(C)C>>CC(C)(C)[Si](OCCC1C(CC1CO[Si](C)(C)C(C)(C)C)N)(C)C | [N-]=[N+]=[N:13][CH:12]1[CH:11]([CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH:15]([CH2:16][O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]1[CH:12]([NH2:13])[CH2:14][CH:15]1[CH... | CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1N=[N+]=[N-] | CC(C)(C)[Si](C)(C)OCCC1C(N)CC1CO[Si](C)(C)C(C)(C)C | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | C1CCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | null | [] | null | null | 0.5 | HOUR | 2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)-1-azidocyclobutane (980 mg, 2.45 mmol), prepared as described in Step D above, was dissolved in 20 mL of methanol and an excess of palladium on carbon was added to the solution under a nitrogen atmosphere. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC1 | Other | [Pd].CO | null | 0.5 | CC(C)(C)[Si](C)(C)OCCC1C(CO[Si](C)(C)C(C)(C)C)CC1N=[N+]=[N-]>[Pd].CO>CC(C)(C)[Si](C)(C)OCCC1C(N)CC1CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-219ddea43bb2403b9dc232f4a67c5dcb | C=CSc1ccccc1.COC(=O)/C=C/C(=O)OC>>COC(=O)C1CC(Sc2ccccc2)C1C(=O)OC | C(=C)SC1=CC=CC=C1.C(\C=C\C(=O)OC)(=O)OC.[Cl-].[Cl-].C(C)[Al+2]>>C1(=CC=CC=C1)SC1C(C(C1)C(=O)OC)C(=O)OC | [CH2:6]=[CH:7][S:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:15]/[C:16](=[O:17])[O:18][CH3:19]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([S:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH:15]1[C:16](=[O:17])[O:18][CH3:19] | C=CSc1ccccc1.COC(=O)/C=C/C(=O)OC | COC(=O)C1CC(Sc2ccccc2)C1C(=O)OC | null | null | CCCCCC.ClCCCl | C-C Coupling | OtherReaction | 5c16026a558496044c7dd74caa20fd1bd37f23b8341135eee4fe11ec335c6003 | 25a34d512903fd4efc0fed33748937a92afa74b7d25d284c50d3bf8b9e5dd2ee | c1ccc(SC2CCC2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[CH;D2;+0:5]=[CH;D2;+0:6]/[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10].[CH2;D1;+0:11]=[CH;D2;+0:12]-[#16:13]-[c:14]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[CH2;D2;+0:11]-[CH;D3;+0:12]-1-[#16:13]-[c:14] | null | [] | null | null | null | null | To a solution of 1.06 g (7.34 mmol) of dimethyl fumarate in 20 mL of dry 1,2-dichloroethane under nitrogen atmosphere, was added with stirring, 7.34 mmol of a 1.0 M solution of ethylaluminum dichloride in hexane. The resultant yellow solution was heated to reflux and a solution of 1.0 g (7.34 mmol) of phenyl vinyl sulf... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Monosulfide.Vinyl | Ester.Ester.Monosulfide | null | C1CCC1 | C1CCC1.c1ccccc1 | null | CCCCCC.ClCCCl | null | null | C=CSc1ccccc1.COC(=O)/C=C/C(=O)OC>CCCCCC.ClCCCl>COC(=O)C1CC(Sc2ccccc2)C1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-70dbc0e828674b098de600e6c942e203 | COC(=O)C1CC(Sc2ccccc2)C1C(=O)OC.O=S(=O)([O-])OO>>COC(=O)C1CC(S(=O)(=O)c2ccccc2)C1C(=O)OC | [K+].S([O-])([O-])(=O)=O.[K+].S(=O)(=O)(OO)[O-].[K+].O.OOS(=O)[O-].[K+].O.C1(=CC=CC=C1)SC1C(C(C1)C(=O)OC)C(=O)OC>>C1(=CC=CC=C1)S(=O)(=O)C1C(C(C1)C(=O)OC)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([S:8][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH:17]1[C:18](=[O:19])[O:20][CH3:21].O=S([O-])(O[OH:10])=[O:9]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH:17]1[C:18](=[O:19])[O:20][CH3:21] | COC(=O)C1CC(Sc2ccccc2)C1C(=O)OC.O=S(=O)([O-])OO | COC(=O)C1CC(S(=O)(=O)c2ccccc2)C1C(=O)OC | null | null | CO.ClC(C)Cl | Oxidation | OtherReaction | 73ca5438c687e7554e6372a79a1d180e809287a4397486487708df09a5fd20e0 | ebe5803abbd530cb5af8bdb9d457c04c55bf786787bd2848bd344ab633fecdcb | O=S(=O)(c1ccccc1)C1CCC1 | O=S(-[O-])(=[O;H0;D1;+0:1])-O-[OH;D1;+0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7](-[S;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:12]>>[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7](-[S;H0;D4;+0:8](=[O;H0;D1;+0:2])(=[O;H0;D1;+0:1])-[c:9](:[c:10]):[c:11])-[C:12] | 94 | [{"value": 94.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1C(C(C1)C(=O)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a vigorously stirred solution of 1.05 g (3.75 mmol) of dimethyl 3-(phenylthio)cyclobutane-1,2-dicarboxylate from Step A in 20 mL of methanol, was added slowly a suspension of 3.46 g (11.25 mmol) of OXONE (a commercially available mixture of sulfuric acid potassium salt and potassium hydrogen peroxymonosulfate) in 20... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfone | null | null | C1CCC1.c1ccccc1 | HO- | CO.ClC(C)Cl | null | 0.5 | COC(=O)C1CC(Sc2ccccc2)C1C(=O)OC.O=S(=O)([O-])OO>CO.ClC(C)Cl>COC(=O)C1CC(S(=O)(=O)c2ccccc2)C1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ba400473a2ca4271ac076e19bab41291 | C=CBr.O=C1C=CC(=O)O1>>COC(=O)C1CC(Br)C1C(=O)OC | C1(\C=C/C(=O)O1)=O.C(C)(=O)C1=CC=CC=C1.C(C)(=O)OCC.C(C)(=O)OCC.O.C(=C)Br>>BrC1C(C(C1)C(=O)OC)C(=O)OC | [CH2:6]=[CH:7][Br:8].[C:3]1(=[O:4])[CH:5]=[CH:9][C:10](=[O:11])[O:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([Br:8])[CH:9]1[C:10](=[O:11])[O:12][CH3:13] | C=CBr.O=C1C=CC(=O)O1 | COC(=O)C1CC(Br)C1C(=O)OC | null | null | null | Functional Group Addition | OtherReaction | e5cbf90970ecb0326ff9d719f3d1a47ebf488ac579f936296c39b10dab529dd1 | 4f77b0786d09c9486b17219f4ba069977b16e1dff1c5f8e08f39cb9f922d30b7 | C1CCC1 | [Br;D1;H0:1]-[CH;D2;+0:2]=[CH2;D1;+0:3].[O;D1;H0:4]=[C:5]1-[CH;D2;+0:6]=[CH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-1>>[Br;D1;H0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH;D3;+0:7](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:11]-[C;D1;H3:12])-[CH;D3;+0:6]-1-[C:5](=[O;D1;H0:4])-[O;H0;D2;+0:10]-[C;D1;H3:13] | 19.5 | [{"value": 19.5, "product": "BrC1C(C(C1)C(=O)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 5 g (51 mmol) of maleic anhydride and 0.5 mL (4 mmol) of acetophenone in 50 mL of ethyl acetate was added to a 100 mL pyrex photochemical reaction vessel. The vessel was sealed and purged with nitrogen for 10 min then cooled with tap water while 13.8 g (129 mmol) of vinyl bromide was being added to the et... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Vinyl | Secondary halide.Ester.Ester | C1=CCOC1 | C1CCC1 | C1CCC1 | Other | null | null | 8 | C=CBr.O=C1C=CC(=O)O1>>COC(=O)C1CC(Br)C1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cfd97c6b760d447ab41eb374f30d7b03 | C=CSc1ccccc1.COC(=O)/C=C\C(=O)OC>>COC(=O)C1C(C(=S)OC)CC1c1ccccc1 | C(\C=C/C(=O)OC)(=O)OC.C(=C)SC1=CC=CC=C1.[Cl-].[Cl-].C(C)[Al+2].CCCCCC>>C1(=CC=CC=C1)C1C(C(C1)C(=S)OC)C(=O)OC | [S:8]([CH:12]=[CH2:11])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O=[C:7](/[CH:6]=[CH:5]\[C:3]([O:2][CH3:1])=[O:4])[O:9][CH3:10]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH:6]([C:7](=[S:8])[O:9][CH3:10])[CH2:11][CH:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CSc1ccccc1.COC(=O)/C=C\C(=O)OC | COC(=O)C1C(C(=S)OC)CC1c1ccccc1 | null | null | C(Cl)Cl.ClCCCl | Heteroatom Alkylation and Arylation | OtherReaction | 9b9ed09135ec7e6e7a29798c9c05a4ff5ef79a948f206959fffaae60990c84f5 | 6c58e17a0727e497a13b218c6c760dc188ee7a3a979a93af34c0bd52b71d43a0 | c1ccc(C2CCC2)cc1 | O=[C;H0;D3;+0:1](-[#8:2]-[C;D1;H3:3])/[CH;D2;+0:4]=[CH;D2;+0:5]\[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].[CH2;D1;+0:10]=[CH;D2;+0:11]-[S;H0;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[C;D1;H3:3]-[#8:2]-[C;H0;D3;+0:1](=[S;H0;D1;+0:12])-[CH;D3;+0:4]1-[CH2;D2;+0:10]-[CH;D3;+0:11](-[c;H0;D3;+0:13](:[c:14]:[c:15... | null | [] | null | null | null | null | To a solution of dimethyl maleate (0.50 mL, 4 mmol) and phenyl vinyl sulfide (0.52 mL, 4 mmol) in 17 mL of 1,2-dichloroethane under nitrogen atmosphere, was added 1 equivalent (4 mL of a 1 M solution in hexane) of ethylaluminum dichloride. The resultant solution was heated at 85° C. for 18 h and then diluted with 75 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Monosulfide.Vinyl | Ester.Ether.Thiocarbonyl | c1ccccc1 | C1CCC1.c1ccccc1 | C1CCC1.c1ccccc1 | Other | C(Cl)Cl.ClCCCl | null | null | C=CSc1ccccc1.COC(=O)/C=C\C(=O)OC>C(Cl)Cl.ClCCCl>COC(=O)C1C(C(=S)OC)CC1c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-48761c7d7d1e44d5995d8941f05c8bb3 | C=CSc1ccccc1.O=C1C=CC(=O)O1>>O=C1OC(=O)C2C(Sc3ccccc3)CC12 | C1(\C=C/C(=O)O1)=O.C(=C)SC1=CC=CC=C1.[Cl-].[Cl-].C(C)[Al+2]>>O=C1C2CC(C2C(O1)=O)SC1=CC=CC=C1 | [CH:7]([S:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[CH2:15].[O:1]=[C:2]1[O:3][C:4](=[O:5])[CH:6]=[CH:16]1>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[CH:6]2[CH:7]([S:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[CH2:15][CH:16]12 | C=CSc1ccccc1.O=C1C=CC(=O)O1 | O=C1OC(=O)C2C(Sc3ccccc3)CC12 | null | null | C(Cl)Cl.ClCCCl | C-C Coupling | OtherReaction | 98ffda9013fbff03e1ca814838858e8a5a770cfd8987bf495f3b231d27cda942 | 419597408ecb4d9e7f97c50b90cc7c04817b398990d488fa33ed3f2de7c774b9 | O=C1OC(=O)C2C(Sc3ccccc3)CC12 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[#16:3]-[c:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10]2-[CH;D3;+0:11]-1-[CH2;D2;+0:1]-[CH;D3;+0:2]-2-[#16:3]-[c:4] | 90.7 | [{"value": 90.7, "product": "O=C1C2CC(C2C(O1)=O)SC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of maleic anhydride (0.39 g, 4 mmol) and phenyl vinyl sulfide (0.52, 4 mmol) in 17 mL of 1,2-dichloroethane under nitrogen, was added 2 mL (0.5 equiv) of ethylaluminum dichloride. The resultant solution was stirred at ambient temperature for 0.5 h and then diluted with 75 mL of methylene chloride. The met... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Vinyl | Monosulfide | C1=CCOC1 | C1CC2COCC12 | c1ccccc1.C1CC2COCC12 | null | C(Cl)Cl.ClCCCl | null | null | C=CSc1ccccc1.O=C1C=CC(=O)O1>C(Cl)Cl.ClCCCl>O=C1OC(=O)C2C(Sc3ccccc3)CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-226d7b5d2766425dab0d0aaeeca1b720 | CC(=O)O[C@@H](C=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C.CC(C)[CH2][Mg][Cl]>>CC(C)C[C@H](O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | C(C(C)C)[Mg]Cl.C(C)(C)(C)OC(=O)N[C@H]([C@H](C=O)OC(C)=O)CC1=CC=CC=C1>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H]([C@H](CC(C)C)O)O | CC(=O)[O:8][C@@H:7]([CH:5]=[O:6])[C@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24].[Cl][Mg][CH2:4][CH:2]([CH3:1])[CH3:3]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17... | CC(=O)O[C@@H](C=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C.CC(C)[CH2][Mg][Cl] | CC(C)C[C@H](O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | null | null | CCOCC.C1CCOC1.CO.O | C-C Coupling | OtherReaction | 5f54c4e65fccd98084a6e40f4bfd9527d67022c981243f8afdf425e5bc03ac12 | 6578779679a50461a804541f986639c94275b5244f2836f24bc151ae868a5ae7 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[Mg]-[Cl]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C@@H;D3;+0:4](-[OH;D1;+0:5])-[CH2;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | null | [] | null | null | 2 | HOUR | The oil prepared in Example 2 was dissolved under nitrogen in 100 mL of dry THF and cooled to -70°. To this solution was added 13 mL (26 mmol) of a 2.0M solution of isobutylmagnesium chloride in ether and the stirred mixture was allowed to warm to room temperature and stir for 2 hrs. After decomposition with MeOH/H2O t... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde.Ester | Secondary alcohol.Secondary alcohol | null | null | c1ccccc1 | HCl.Mg | CCOCC.C1CCOC1.CO.O | null | 2 | CC(=O)O[C@@H](C=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C.CC(C)[CH2][Mg][Cl]>CCOCC.C1CCOC1.CO.O>CC(C)C[C@H](O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b9a26e58d0284adca803900d4bbf0d32 | C1CCNC1.Cc1cc(Br)c([N+](=O)[O-])cc1[N+](=O)[O-]>>Cc1cc(N2CCCC2)c([N+](=O)[O-])cc1[N+](=O)[O-] | BrC=1C(=CC(=C(C1)C)[N+](=O)[O-])[N+](=O)[O-].N1CCCC1>>CC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])N2CCCC2 | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1.Br[c:4]1[cH:3][c:2]([CH3:1])[c:15]([N+:16](=[O:17])[O-:18])[cH:14][c:10]1[N+:11](=[O:12])[O-:13]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9]2)[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | C1CCNC1.Cc1cc(Br)c([N+](=O)[O-])cc1[N+](=O)[O-] | Cc1cc(N2CCCC2)c([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:2]:[c:3] | null | [] | null | null | null | null | A mixture of 5-bromo-2,4-dinitrotoluene (2.61 g, 10 mmol) and pyrrolidine (2.49 g, 35 mmol) was heated at 90°-100° C. for 2 hours. The resulting dark brown oil was combined with cracked ice and the precipitated solids filtered off, washed with water, and vacuum dried. Purification was carried out by flash chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HBr | null | null | null | C1CCNC1.Cc1cc(Br)c([N+](=O)[O-])cc1[N+](=O)[O-]>>Cc1cc(N2CCCC2)c([N+](=O)[O-])cc1[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-981e6b6f4d594c2eb9e7f2100fc60f0c | CC(=O)Nc1cc2nc3n(c2cc1C)CCC3.O=[N+]([O-])O>>CC(=O)Nc1c(C)cc2c(nc3n2CCC3)c1[N+](=O)[O-] | C([O-])(O)=O.[Na+].[N+](=O)(O)[O-].S(O)(O)(=O)=O.C(C)(=O)NC1=CC2=C(N3C(=N2)CCC3)C=C1C>>C(C)(=O)NC1=C(C2=C(N3C(=N2)CCC3)C=C1C)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]2[c:10]([n:11][c:12]3[n:13]2[CH2:14][CH2:15][CH2:16]3)[cH:17]1.O[N+:18](=[O:19])[O-:20]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]2[c:10]([n:11][c:12]3[n:13]2[CH2:14][CH2:15][CH2:16]3)[c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)Nc1cc2nc3n(c2cc1C)CCC3.O=[N+]([O-])O | CC(=O)Nc1c(C)cc2c(nc3n2CCC3)c1[N+](=O)[O-] | null | null | C(Cl)(Cl)Cl | Functional Group Addition | Aromatic nitration with HNO3 | e610d116336568a4b154d6df06dd039399a3bbe0b7f6053414cbf5e29d39d23b | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2c(c1)nc1n2CCC1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[cH;D2;+0:9]:[c:10](-[#7:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]):[c:15]:[c:16]:[c:17]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[c:17]:1:[c:16]:[c:15]:[c:10](-[#7:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]):[c;H0;D3;+0:9]:2-[N+;H0;D3:1](-[O;-... | null | [] | 0 | CELSIUS | 5 | MINUTE | To a mixture of 5.4 mL of fuming nitric acid and 0.6 mL of concentrated sulfuric acid, chilled at 0° C., was added 600 mg (2.61 mmol) of 20. The reaction mixture was stirred at 0° C. for 5 min and then poured into a mixture of 20 g of cracked ice and 30 mL of chloroform. The mixture was neutralized with saturated aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)nc1n2CCC1 | c1ccc2c(c1)nc1n2CCC1 | c1ccc2c(c1)nc1n2CCC1 | HO- | C(Cl)(Cl)Cl | 0 | 0.083333 | CC(=O)Nc1cc2nc3n(c2cc1C)CCC3.O=[N+]([O-])O>C(Cl)(Cl)Cl>CC(=O)Nc1c(C)cc2c(nc3n2CCC3)c1[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-461d76bc7b794e33b5c526fa6f430a5a | CCOC(=O)CCCCBr.O/N=C1\c2ccccc2CCC1n1ccnc1>>CCOC(=O)CCCCO/N=C1\c2ccccc2CCC1n1ccnc1 | [H-].[Na+].C(C)OC(CCCCBr)=O.N1(C=NC=C1)C1/C(/C2=CC=CC=C2CC1)=N/O.CCCCC>>C(C)OC(CCCCO/N=C\1/C(CCC2=CC=CC=C12)N1C=NC=C1)=O | Br[CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:10]/[N:11]=[C:12]1\[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[CH2:19][CH2:20][CH:21]1[n:22]1[cH:23][cH:24][n:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][O:10]/[N:11]=[C:12]1\[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[CH2:19... | CCOC(=O)CCCCBr.O/N=C1\c2ccccc2CCC1n1ccnc1 | CCOC(=O)CCCCO/N=C1\c2ccccc2CCC1n1ccnc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f17bbd9c17b3a875a5aa1550ae4713b0ba603c9d3f46ba0999fc0e89cd423a21 | 4d77d2b34a9e45ba02341fbaa1023b2e18d467b26d20c41a36320fe71f49b6cc | N=C1c2ccccc2CCC1n1ccnc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]/[C:5](=[#7:6]/[OH;D1;+0:7])-[c:8]>>[C:4]/[C:5](=[#7:6]/[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3])-[c:8] | null | [] | null | null | 2 | HOUR | (+-)-(E)-2-(1H-imidazol-1-yl)-1,2,3,4-tetrahydronaphtalen-1-one oxime (500 mg; 2.2 mmoles) dissolved in dry DMF (27 ml) is added, under dry nitrogen atmosphere, to a pentane-washed sodium hydride suspension (160 mg NaH 55%; 3.6 mmoles), in dry DMF (10 ml). The resulting reaction mixture is stirred at r.t. for 2 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Oxime | null | null | null | c1ccc2c(c1)CCCC2.c1c[nH]cn1 | HBr | CN(C)C=O | null | 2 | CCOC(=O)CCCCBr.O/N=C1\c2ccccc2CCC1n1ccnc1>CN(C)C=O>CCOC(=O)CCCCO/N=C1\c2ccccc2CCC1n1ccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ec948c710b104c45b379cfa5db96a444 | CCO.NO.O=C1c2ccccc2OC(c2ccccc2)C1n1ccnc1>>CCOC(=O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 | C1(=CC=CC=C1)C1OC2=C(C(C1N1C=NC=C1)=O)C=CC=C2.Cl.NO.C(C)O>>C(C)OC(CCCCCO\N=C\1/C(C(OC2=C1C=CC=C2)C2=CC=CC=C2)N2C=NC=C2)=O | [CH3:1][CH2:2][OH:3].[OH:11][NH2:12].[cH:4]1[cH:23][c:22]([CH:21]2[O:20][c:19]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[C:13](=[O:5])[CH:28]2[n:29]2[cH:30][cH:31][n:32][cH:33]2)[cH:27][cH:26][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11]/[N:12]=[C:13]1/[c:14]2[cH:15][cH:16][cH:17][cH:... | CCO.NO.O=C1c2ccccc2OC(c2ccccc2)C1n1ccnc1 | CCOC(=O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | fae9f856a9f9c1d9c53ed51f52a7495031b7e01844e7ba054ee2540ef0f6e264 | 2b81e1c79b0930cb310162e7f6642408f3f24947e2166ae9a97d74ef90c9810e | N=C1c2ccccc2OC(c2ccccc2)C1n1ccnc1 | [#7;a:1]-[C:2]1-[C:3](-[c:4]2:[c:5]:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:2)-[#8:10]-[c:11]:[c:12](:[c:13])-[C;H0;D3;+0:14]-1=[O;H0;D1;+0:15].[C;D1;H3:16]-[C:17]-[OH;D1;+0:18].[NH2;D1;+0:19]-[OH;D1;+0:20]>>[#7;a:1]-[C:2]1-[C:3](-[c:4]2:[c:5]:[c:6]:[cH;D2;+0:7]:[c:21]:[cH;D2;+0:9]:2)-[#8:10]-[c:11]:[c:12](:[c:13]... | null | [] | null | null | null | null | As an example the intermediate oxime used as starting material can be prepared as follows: (+-)-2-phenyl-3-(1H-imidazol-1-yl)-2,3-dihydro-4H-benzopyran-4-one[J. Het. Chem. 21,311,(1984)], (4 g.; 0.014 moles), is dissolved in pyridine, and hydroxylamine hydrochloride (2.4 g.; 0.034 moles) dissolved in ethanol (20 ml), i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary amine | Ester | c1ccccc1.c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1ccccc1 | c1ccc2c(c1)CCCO2.c1ccccc1.c1c[nH]cn1 | Other | N1=CC=CC=C1 | null | null | CCO.NO.O=C1c2ccccc2OC(c2ccccc2)C1n1ccnc1>N1=CC=CC=C1>CCOC(=O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c80aa69c1d3242f49b34a59f1fc7f324 | CCOC(=O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1>>O=C(O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 | C(C)OC(CCCCCO\N=C\1/C(C(OC2=C1C=CC=C2)C2=CC=CC=C2)N2C=NC=C2)=O.C[O-].[Na+].C(C)(=O)O>>C1(=CC=CC=C1)C1OC2=C(/C(/C1N1C=NC=C1)=N/OCCCCCC(=O)O)C=CC=C2 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9]/[N:10]=[C:11]1/[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[O:18][CH:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH:26]1[n:27]1[cH:28][cH:29][n:30][cH:31]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9]/[N:10]=[C:11]1/[c:12]2[cH:13][cH:14][cH... | CCOC(=O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 | O=C(O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 | null | null | O.CO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | N=C1c2ccccc2OC(c2ccccc2)C1n1ccnc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 67.6 | [{"value": 67.6, "product": "C1(=CC=CC=C1)C1OC2=C(/C(/C1N1C=NC=C1)=N/OCCCCCC(=O)O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 28 | HOUR | (+-)-(Z)-Ethyl-6-[[2-phenyl-3-(1H-imidazol-1-yl)-2,3-dihydro-4H-benzopyranylidene]aminoxy]hexanoate (300 mg; 0.67 mmoles) is dissolved in methanol-water (5:2; 7 ml), and to this solution sodium methylate (90 mg; 1.61 mmoles) is added portion-wise at 0° C. The resulting solution is stirred at r.t. for 28 hrs., then dilu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CCCO2.c1ccccc1.c1c[nH]cn1 | Other | O.CO.O | null | 28 | CCOC(=O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1>O.CO.O>O=C(O)CCCCCO/N=C1/c2ccccc2OC(c2ccccc2)C1n1ccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c3a3a61a8198408ba4cdc90797c22908 | CC(=O)Cl.CC1(C)CCC(C)(C)c2ccccc21>>CC(=O)c1ccc2c(c1)C(C)(C)CCC2(C)C | [Cl-].[Al+3].[Cl-].[Cl-].CC1(CCC(C2=CC=CC=C12)(C)C)C.C(C)(=O)Cl>>CC1(CCC(C2=CC(=CC=C12)C(C)=O)(C)C)C | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][C:15]2([CH3:16])[CH3:17]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][C:15]2([CH3:16])[CH3:17] | CC(=O)Cl.CC1(C)CCC(C)(C)c2ccccc21 | CC(=O)c1ccc2c(c1)C(C)(C)CCC2(C)C | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 6e0b00c9f9c0959ad91deeb078de9a4a88037b2bb5dd67980650a843b3016249 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(c1)CCCC2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 2 | HOUR | A suspension of 3.45 g (25.9 mmol) aluminum chloride in 15 ml methylene chloride was cooled under argon in an ice/salt bath and treated while stirring with a mixture of 4 g (21.2 mmol) 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro naphthalene (from Example 2) and 1.94 g (24.7 mmol) acetylchloride via a dropping funnel over a ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HCl | C(Cl)Cl | null | 2 | CC(=O)Cl.CC1(C)CCC(C)(C)c2ccccc21>C(Cl)Cl>CC(=O)c1ccc2c(c1)C(C)(C)CCC2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f6572f03311442eaabd3eed776db3701 | CC(=O)c1cc2c(cc1C)C(C)(C)CCC2(C)C>>C#Cc1cc2c(cc1C)C(C)(C)CCC2(C)C | C(C)(C)[N-]C(C)C.[Li+].CC1(CCC(C2=CC(=C(C=C12)C)C(C)=O)(C)C)C.P(=O)(OCC)(OCC)Cl.C(C)(C)NC(C)C.C(C)(C)NC(C)C.C(CCC)[Li].C(CCC)[Li]>>CC1(CCC(C2=CC(=C(C=C12)C)C#C)(C)C)C | O=[C:2]([CH3:1])[c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][C:15]2([CH3:16])[CH3:17]>>[CH:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][C:15]2([CH3:16])[CH3:17] | CC(=O)c1cc2c(cc1C)C(C)(C)CCC2(C)C | C#Cc1cc2c(cc1C)C(C)(C)CCC2(C)C | null | null | CCCCCC.O1CCCC1 | Functional Group Interconversion | OtherReaction | df4f03d2116228d20bc5d8403092a8dd982f38312b775d7fadf08d78c364384d | 70d06bbe4d921df55900f4b8f7e6e878b9de0b1a93bf34dcf81c33c29d9b3281 | c1ccc2c(c1)CCCC2 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[CH;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | -78 | CELSIUS | 1.25 | HOUR | To a stirred solution of 794.2 mg (7.8486 mmol) diisopropylamine in 7 ml dry tetrahydrofuran under argon at -78° C. was added dropwise 4.9 ml of 1.6M (7.84 mmol) n-butyllithium in hexane. This solution was stirred at -78° C. for 1.25 hours and then treated via a double ended needle with a solution of 1.9 g (7.7749 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkyne | null | null | c1ccc2c(c1)CCCC2 | HO- | CCCCCC.O1CCCC1 | -78 | 1.25 | CC(=O)c1cc2c(cc1C)C(C)(C)CCC2(C)C>CCCCCC.O1CCCC1>C#Cc1cc2c(cc1C)C(C)(C)CCC2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7d6fedb6c5194b37b83c946407de6f1b | CCO.O=C(O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(Cl)nc1 | ClC1=NC=C(C(=O)O)C=C1.C(C)O.C1(CCCCC1)N=C=NC1CCCCC1.CN(C)C1=NC=CC=C1>>ClC1=NC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1 | CCO.O=C(O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(Cl)nc1 | null | null | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g 0.03 mol) dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and residue subjected to flash ch... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | null | CCO.O=C(O)c1ccc(Cl)nc1>C(Cl)Cl>CCOC(=O)c1ccc(Cl)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ce06cac6a0cb4076bfda0e623367afbb | C#Cc1ccc2c(c1)C(C)(C)CCC2(C)C.CCOC(=O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 | ClC1=NC=C(C(=O)OCC)C=C1.CC1(CCC(C2=CC(=CC=C12)C#C)(C)C)C.C(CCC)[Li]>>CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1)C | [CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]2([CH3:24])[CH3:25].Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:27][n:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]... | C#Cc1ccc2c(c1)C(C)(C)CCC2(C)C.CCOC(=O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 | null | null | C1CCOC1.CCCCCC | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccn1)c1ccc2c(c1)CCCC2 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 15 | MINUTE | The reaction vessels used in this procedure were flame dried under vacuum and all operations were carried out in an oxygen-free argon or nitrogen atmosphere. To a solution of 417.6 mg 1.9667 mmol) of 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-ethynylnapthalene in 3 ml of dry tetrahydrofuron (THF) at 0° C. was added dropw... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCCC2 | HCl | C1CCOC1.CCCCCC | 0 | 0.25 | C#Cc1ccc2c(c1)C(C)(C)CCC2(C)C.CCOC(=O)c1ccc(Cl)nc1>C1CCOC1.CCCCCC>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5874430b1694beea4c83d85fd26590c | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1>>CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)O)cn3)ccc21 | CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1)C.[OH-].[K+]>>CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C(=O)O)C=C1)C | CC[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([C:13]#[C:12][c:11]2[cH:10][c:9]3[c:25]([cH:24][cH:23]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3([CH3:7])[CH3:8])[n:22][cH:21]1)=[O:19]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([C:12]#[C:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[O... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)O)cn3)ccc21 | null | null | C(C)O.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(#Cc1ccccn1)c1ccc2c(c1)CCCC2 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 18 | HOUR | Absolute ethanol was degassed by applying a vacuum while simultaneously bubbling nitrogen through it. A solution of 188 mg (0.5201 mmol) ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronapth-2-yl)ethynyl]-nicotinoate in 2 ml absolute ethanol was treated with 800 ml of a 1.65M (1.32 mmol) solution of potassium hydroxi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CCCC2.c1ccncc1 | Other | C(C)O.O | null | 18 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1>C(C)O.O>CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)O)cn3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bbaaf1b0e141462ea39d5493141308d6 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1>>CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(CO)cn3)ccc21 | CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].C(C)(=O)OCC.[Cl-].[NH4+]>>CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C=C1)CO)C | CCO[C:18]([c:17]1[cH:16][cH:15][c:14]([C:13]#[C:12][c:11]2[cH:10][c:9]3[c:24]([cH:23][cH:22]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3([CH3:7])[CH3:8])[n:21][cH:20]1)=[O:19]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([C:12]#[C:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(CO)cn3)ccc21 | null | null | CCOCC.C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C(#Cc1ccccn1)c1ccc2c(c1)CCCC2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]-[C:8]#[C:9]>>[C:9]#[C:8]-[c:7]:[#7;a:6]:[c:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | -65 | CELSIUS | 1 | HOUR | A 250 ml 3-necked flask is fitted with a stirrer, a dropping funnel, a nitrogen inlet and a thermometer. In the flask is placed a solution of 379.5 mg (10 mmol) of lithium aluminum hydride in 30 ml of dry diethyl ether. The solution is cooled to -65° C. under nitrogen and a solution of 3.6148 g (10 mmol) of ethyl 6-[2-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2c(c1)CCCC2.c1ccncc1 | HO- | CCOCC.C(C)OCC | -65 | 1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1>CCOCC.C(C)OCC>CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(CO)cn3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e7caa121743b481dbe432fafda8163d7 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(CO)cn3)ccc21>>CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C=O)cn3)ccc21 | C(C)N(CC)CC.CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C=C1)CO)C.C(C(=O)Cl)(=O)Cl.CS(=O)C>>CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C=C1)C=O)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([C:12]#[C:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][n:21]3)[cH:22][cH:23][c:24]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([C:12]#[C:13][c:14]3[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][n:... | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(CO)cn3)ccc21 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C=O)cn3)ccc21 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C(#Cc1ccccn1)c1ccc2c(c1)CCCC2 | [C:1]#[C:2]-[c:3]:[#7;a:4]:[c:5]:[c:6](-[CH2;D2;+0:7]-[OH;D1;+0:8]):[c:9]>>[C:1]#[C:2]-[c:3]:[#7;a:4]:[c:5]:[c:6](-[CH;D2;+0:7]=[O;H0;D1;+0:8]):[c:9] | null | [] | -60 | CELSIUS | 10 | MINUTE | A solution of 1.396 g (11 mmol) of freshly distilled oxalyl chloride in 25 ml of methylene chloride is placed in a 4-necked flask equipped with a stirrer, a thermometer and two pressure-equalizing addition funnels fitted with drying tubes. The solution is cooled to -60° C. and then treated dropwise with a solution of 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2c(c1)CCCC2.c1ccncc1 | null | C(Cl)Cl | -60 | 0.166667 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(CO)cn3)ccc21>C(Cl)Cl>CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C=O)cn3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2df1b2c03444a26b30ca461acdd85d7 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C=O)cn3)ccc21>>CCC(O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 | CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C=C1)C=O)C.C(C)[Mg]Br>>CC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=NC=C(C=C1)C(CC)O)C | [CH:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[C:17]([CH3:18])([CH3:19])[CH2:20][CH2:21][C:22]3([CH3:23])[CH3:24])[n:25][cH:26]1>>[CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[C:17]([CH3:18])([CH3:19])[CH2:20]... | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C=O)cn3)ccc21 | CCC(O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 | null | null | CCOCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | C(#Cc1ccccn1)c1ccc2c(c1)CCCC2 | [C:1]#[C:2]-[c:3]:[#7;a:4]:[c:5]:[c:6](-[CH;D2;+0:7]=[O;H0;D1;+0:8]):[c:9]>>[C:1]#[C:2]-[c:3]:[#7;a:4]:[c:5]:[c:6](-[CH;D3;+0:7](-[OH;D1;+0:8])-[C:10]-[C;D1;H3:11]):[c:9] | null | [] | null | null | 1 | HOUR | Four ml of a 3M (12 mmol) solution of ethylmagnesium bromide in ether is placed in a 3-necked flask fitted with a mechanical stirrer, a reflux condenser protected by a drying tube and a pressure-equalizing dropping funnel protected by a drying tube. The flask is cooled in an ice-bath and a solution of 3.174 g (10 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccncc1.c1ccc2c(c1)CCCC2 | Other | CCOCC | null | 1 | CC1(C)CCC(C)(C)c2cc(C#Cc3ccc(C=O)cn3)ccc21>CCOCC>CCC(O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3(C)C)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-db15010c44024ab7b6dce45226590289 | COC(=O)CCC=O.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COC=CCCC(=O)OC | O.[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=CCCC(=O)OC.C(CCC)[Li]>>COC=CCCC(=O)OC | O=[CH:4][CH2:5][CH2:6][C:7](=[O:8])[O:9][CH3:10].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][O:2][CH3:1])cc1>>[CH3:1][O:2][CH:3]=[CH:4][CH2:5][CH2:6][C:7](=[O:8])[O:9][CH3:10] | COC(=O)CCC=O.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC=CCCC(=O)OC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 1b762435fe6b580b808a6e9f0dae00ddd254c0b88d607d21a223e11776d2e3a4 | bf4569804906d66c98adaac7df334e96eee508d45c26c621eb5069c3e4f1df77 | null | O=[CH;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C;D1;H3:7]-[#8:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH;D2;+0:1]=[CH;D2;+0:9]-[#8:8]-[C;D1;H3:7] | 607.8 | [{"value": 607.8, "product": "COC=CCCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 34.3 g (0.1 mole) methoxymethyltriphenylphosphonium chloride was suspended in 100 ml dry tetrahydrofuran and cooled to -78° C. under argon. 75 ml (0.1 mole) n-butyllithium solution in hexane was added and the solution allowed to warm to room temperature. After cooling to -78° C. 12.1 g (0.0105 moles) methyl 4-oxobutano... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Ether | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | CCCCCC.O1CCCC1 | -78 | null | COC(=O)CCC=O.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>CCCCCC.O1CCCC1>COC=CCCC(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6382314ae13e449e8e31eb63b6d50308 | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1C(SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.SC1=CC=C(C#N)C=C1>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[CH:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][c:16]([C:17]... | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | null | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+] | C(C)#N | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 17 | [{"value": 17.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.5, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A suspension of 625 mg (1.76.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 200 mg (1.48.10-3 mol) of 4-mercaptobenzonitrile and a 400 pm molecular sieve in 10 ml of acetonitrile is stirred in the presence of 605 mg (4.4.10-3 mol) of zinc chloride and 310 mg (1.8.10-3 mol) of silver imidazolate, in the... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(C)#N | 50 | null | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1ccc(S)cc1>[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(C)#N>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-783281c6407248d1a55de54558cee7a5 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.N#Cc1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | ClC(C(O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1)=N)(Cl)Cl.SC1=CC=C(C#N)C=C1>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | N=C(O[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1)C(Cl)(Cl)Cl.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.N#Cc1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | null | [Cl-].[Zn+2].[Cl-] | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 7c07014415d74e2e131b010ffcc25fdad90565eadd3ecae2c758d81a81f8b48b | cd3e604fca59805deffdc9eb316e9a69d7b42764ff09e348369deb91b52f9839 | c1ccc(S[C@H]2CCCCS2)cc1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 23 | [{"value": 23.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 192 mg (0.44.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 71 mg (0.52.10-3 mol) of 4-mercaptobenzonitrile, 20 mg (0.15.10-3 mol) of zinc chloride and a 400 pm sieve in 2 ml of acetonitrile is stirred for 4 h under an inert atmosphere. The reaction mixture is then filter... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Aromatic thiol.Monosulfide | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HCl | [Cl-].[Zn+2].[Cl-].C(C)#N | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.N#Cc1ccc(S)cc1>[Cl-].[Zn+2].[Cl-].C(C)#N>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c325c2e4bd414d69a18ffb5e8f24076c | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.SC1=CC=C(C#N)C=C1>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][c:16]([C:1... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 64 | [{"value": 64.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 18 | HOUR | A suspension of 16.9 g (47.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6 g (43.10-3 mol) of 4-mercaptobenzonitrile and 3.5 g (43.10-3 mol) of zinc oxide (ZnO) in 120 ml of anhydrous toluene and 120 ml of acetonitrile is stirred under an inert atmosphere, in the presence of a molecular sieve (1 mm)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2].C(C)#N.C1(=CC=CC=C1)C | 50 | 18 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)cc1>[O-2].[Zn+2].C(C)#N.C1(=CC=CC=C1)C>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-df939d720ab54ac1ba13f03f130484a8 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O>>N#Cc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C#N | CC(=O)[O:12][C@@H:11]1[CH2:10][S:9][C@@H:8]([S:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]2)[C@H:15]([O:16]C(C)=O)[C@H:13]1[O:14]C(C)=O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([S:7][C@@H:8]2[S:9][CH2:10][C@@H:11]([OH:12])[C@H:13]([OH:14])[C@H:15]2[OH:16])[cH:17][cH:18]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O | N#Cc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(S[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 89.7 | [{"value": 89.7, "product": "S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under a nitrogen atmosphere, 8.5 g (21.10-3 mol) of 4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 1a) are suspended in 100 ml of methanol, and 2 ml of sodium methylate (8% w/v of Na in methanol) are then added. The reaction medium is stirred at room temperature until the starting material has ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2)SC[C@H]1OC(C)=O>CO>N#Cc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6e155a0fcdfe4261a9d6e2ec6bcd8028 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.[N+](=O)([O-])C1=CC=C(C=C1)S.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[CH2:23][S:22]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 66 | [{"value": 66.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 6 g (38.10-3 mol) of 4-nitrobenzenethiol, 10.7 g (42.10-3 mol) of mercuric cyanide, Hg(CN)2, and 15.1 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 10.8 g (yield: 66%) of the expected product are obtained.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-62639ba3ea8e47aa90d2c7105c41edd9 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O | [N+](=O)([O-])C1=CC=C(C=C1)S.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[CH2:23][S:22]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 79 | [{"value": 79.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 6 g (38.10-3 mol) of 4-nitrobenzenethiol, 15.1 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 3.2 g (39.10-3 mol) of zinc oxide (ZnO), 13 g (yield: 79%) of the expected product are obtained after precipitation in ether.
C... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(S)cc1>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-69dfd454486f4733968831d54991e21b | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccc2ccccc2c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc3ccccc3c2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.C1=C(C=CC2=CC=CC=C12)S.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC3=CC=CC=C3C=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[CH2:24][S:23]1.[SH:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccc2ccccc2c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc3ccccc3c2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc2cc(S[C@H]3CCCCS3)ccc2c1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 40 | [{"value": 40.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC3=CC=CC=C3C=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC3=CC=CC=C3C=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 6.8 g (42.4.10-3 mol) of naphthalene-2-thiol, 10.8 g (42.4.10-3 mol) of mercuric cyanide, Hg(CN)2, and 12 g (33.2.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 5.84 g (yield: 40%) of the expected product are obtained.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccc2ccccc2c1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccc2ccccc2c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc3ccccc3c2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0e5f513459a84d2786a08726e0e9d65d | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.FC(C1=CC=C(C=C1)S)(F)F.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[CH2:24][S:23]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 40 | [{"value": 40.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 5.58 g (32.10-3 mol) of 4-tri-fluoromethylbenzenethiol, 8.87 g (35.10-3 mol) of mercuric cyanide, Hg(CN)2, and 12.3 g (35.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6.2 g (yield: 40%) of the expected product are obtained.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6e968d420acc44f5a9c97e2954212c9c | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccc(S)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O | FC(C1=CC=C(C=C1)S)(F)F.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[CH2:24][S:23]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccc(S)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 48 | [{"value": 48.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 5.6 g (32.10-3 mol) of 4trifluoromethylbenzenethiol, 12.3 g (35.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 2.55 g (32.10-3 mol) of zinc oxide (ZnO), 7.4 g (yield: 48%) of the expected product are obtained after precipitatio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccc(S)cc1>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b26089eaf91d4f27b4272b0ec41c29a8 | CN(C)C(=S)Cl.N#Cc1cccc(O)c1>>CN(C)C(=S)Oc1cccc(C#N)c1 | [OH-].[K+].OC=1C=C(C#N)C=CC1.CN(C(=S)Cl)C>>CN(C(OC1=CC(=CC=C1)C#N)=S)C | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[S:5].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14]1>>[CH3:1][N:2]([CH3:3])[C:4](=[S:5])[O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14]1 | CN(C)C(=S)Cl.N#Cc1cccc(O)c1 | CN(C)C(=S)Oc1cccc(C#N)c1 | null | null | null | Acylation | Schotten-Baumann to ester | 085dbfd01da3f23432eb68a0c9926226856f71cf39acf52aeac55f77c5219807 | 42727264d4762866b627891a642b01ccb211aee4f45c12cd2bb71e89549be2cf | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[S;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[S;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | If the procedure described in Preparation XI is followed starting from 15 g (126.10-3 mol) of 3-hydroxybenzonitrile, 17.9 g (145.10-3 mol) of dimethylthiocarbamoyl chloride and 7.4 g (132.10-3 mol) of potassium hydroxide, 29 g (quantitative yield) of the expected product are obtained.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Thioamide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | null | null | null | CN(C)C(=S)Cl.N#Cc1cccc(O)c1>>CN(C)C(=S)Oc1cccc(C#N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e160f17724b945938456d36adf413951 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(S)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.SC=1C=C(C#N)C=CC1.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH:16][c:1... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(S)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | null | [] | null | null | null | null | If the procedure described in Preparation I is followed starting from 9.3 g (67.10-3 mol) of 3-mercaptobenzonitrile, 18 g (73.10-3 mol) of mercuric cyanide, Hg(CN)2, and 26.14 g (73.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8.55 g of the expected product are obtained.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(S)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3797a11312aa4e1d97071f5559443167 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(S)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O | SC=1C=C(C#N)C=CC1.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH:16][c:1... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(S)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 31 | [{"value": 31.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.8, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 10.3 g (74.1.10-3 mol) of 3-mercaptobenzonitrile, 28.94 g (81.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.05 g (74.3.10-3 mol) of zinc oxide (ZnO), 9.6 g (yield: 31%) of the expected product are obtained.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(S)c1>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0e3bf4991a3f466d9c41ae0105fc4554 | CN(C)C(=S)Cl.N#Cc1ccccc1O>>CN(C)C(=S)Oc1ccccc1C#N | [OH-].[K+].OC1=C(C#N)C=CC=C1.CN(C(=S)Cl)C>>CN(C(OC1=C(C=CC=C1)C#N)=S)C | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[S:5].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]#[N:14]>>[CH3:1][N:2]([CH3:3])[C:4](=[S:5])[O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]#[N:14] | CN(C)C(=S)Cl.N#Cc1ccccc1O | CN(C)C(=S)Oc1ccccc1C#N | null | null | null | Acylation | Schotten-Baumann to ester | 085dbfd01da3f23432eb68a0c9926226856f71cf39acf52aeac55f77c5219807 | 42727264d4762866b627891a642b01ccb211aee4f45c12cd2bb71e89549be2cf | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[S;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[S;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 94 | [{"value": 94.0, "product": "CN(C(OC1=C(C=CC=C1)C#N)=S)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation XVI is followed starting from 15 g (126.10-3 mol) of 2-hydroxybenzonitrile, 17.9 g (145.10-3 mol) of dimethylthiocarbamoyl chloride and 7.4 g (126.10-3 mol) of potassium hydroxide, 24.1 g (yield: 94%) of the expected product are obtained.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Thioamide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | null | null | null | CN(C)C(=S)Cl.N#Cc1ccccc1O>>CN(C)C(=S)Oc1ccccc1C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9b0f85be4c6140d5896fab7059cbf008 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.SC1=C(C#N)C=CC=C1.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]#[N:20]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH:16][cH:17... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1S | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 50 | [{"value": 50.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 9.70 g (72.10-3 mol) of 2-mercaptobenzonitrile, 19.45 g (77.10-3 mol) of mercuric cyanide, Hg(CN)2, and 27.4 g (77.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 14.7 g (yield: 50%) of the expected product are obtained.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-021666c894ee4cbba7a64470dd7059e7 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O | SC1=C(C#N)C=CC=C1.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:23]([O:24][C:25]([CH3:26])=[O:27])[CH2:22][S:21]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]#[N:20]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH:16][cH:17... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1S | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 60 | [{"value": 60.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 10.7 g (79.2.10-3 mol) of 2-mercaptobenzonitrile, 30.2 g (85.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.3 g (77.4.10-3 mol) of zinc oxide (ZnO), 19.3 g (yield: 60%) of the expected product are obtained after crystallizati... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1S>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9c45a27a7f934ba4b93e4d1e32569393 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.[N+](=O)([O-])C1=C(C=CC=C1)S.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[CH2:23][S:22]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1S | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 48 | [{"value": 48.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 6 g (38.7.10-3 mol) of 2-nitrobenzenethiol, 10.75 g (42.5.10-3 mol) of mercuric cyanide, Hg(CN)2, and 15.12 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8 g (yield: 48%) of the expected product are obtained.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3e2d878ec29b4bfc9297a97ac3acc1b2 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O | [N+](=O)([O-])C1=C(C=CC=C1)S.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[CH2:23][S:22]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1S | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 58.5 | [{"value": 58.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.5, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | If the procedure described in Preparation IV is followed starting from 6.1 g (39.3.10-3 mol) of 2-nitrobenzenethiol, 15.40 g (43.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 3.68 g (45.2.10-3 mol) of zinc oxide (ZnO), 9.87 g (yield: 58%) of the expected product are obtained.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1S>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0ca6092933ea4a7da1ca782d6487ff3a | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccccc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O | C1(=CC=CC=C1)S.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC=CC=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:21]([O:22][C:23]([CH3:24])=[O:25])[CH2:20][S:19]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[S... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccccc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 52.3 | [{"value": 52.3, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=CC=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 4 g (36.3.10-3 mol) of benzenethiol, 14 g (39.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-xylopyranosyl bromide and 10 g (39.10-3 mol) of mercuric cyanide (Hg(CN)2), 7.3 g of the expected product are obtained after crystallization from ether.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccccc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e8f938242b2b48989838b82c5425b8d6 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccccc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O | C1(=CC=CC=C1)S.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC=CC=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:21]([O:22][C:23]([CH3:24])=[O:25])[CH2:20][S:19]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[S... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccccc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 32.29 | [{"value": 32.29, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=CC=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=CC=C2)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 4 g (36.3.10-3 mol) of benzenethiol, 15 g (42.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 3 g (36.8.10-3 mol) of zinc oxide (ZnO), 4.5 g (yield: 32.29%) of the expected product are obtained after crystallization from ether... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.Sc1ccccc1>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a168521407ce43298f3e0fd66fa637a9 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.COc1cc(S)cc(OC)c1OC>>COc1cc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc(OC)c1OC | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.COC=1C=C(C=C(C1OC)OC)S.[Hg](C#N)C#N.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC(=C(C(=C2)OC)OC)OC)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@H:7]1[S:8][CH2:9][C@@H:10]([O:11][C:12]([CH3:13])=[O:14])[C@H:15]([O:16][C:17]([CH3:18])=[O:19])[C@H:20]1[O:21][C:22]([CH3:23])=[O:24].[CH3:1][O:2][c:3]1[cH:4][c:5]([SH:6])[cH:25][c:26]([O:27][CH3:28])[c:29]1[O:30][CH3:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][C@@H:7]2[S:8][CH2:9][C@@H:10]([O:11][C:12]([CH3:13])=[O... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.COc1cc(S)cc(OC)c1OC | COc1cc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc(OC)c1OC | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[#16:2]-[C:3] | 28 | [{"value": 28.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=C(C(=C2)OC)OC)OC)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 11.35 g (57.10-3 mol) of 3,4,5-trimethoxybenzenethiol, 14.32 g (57.10-3 mol) of mercuric cyanide, Hg(CN)2, and 22.15 g (62.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 7.52 g (yield: 28%) of the expected product are obtained.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | c1ccccc1.C1CCSCC1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.COc1cc(S)cc(OC)c1OC>>COc1cc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc(OC)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86b0005ef8c14e33b6bf5c9a49e82eb2 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1cccc(S)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O | [N+](=O)([O-])C=1C=C(C=CC1)S.[Hg](C#N)C#N.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[CH2:23][S:22]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15][... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1cccc(S)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 27 | [{"value": 27.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.9, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | If the procedure described in Preparation I is followed starting from 10 g (64.5.10-3 mol) of 3-nitrobenzenethiol, 16.29 g (64.5.10-3 mol) of mercuric cyanide (Hg(CN)2) and 25.2 g (70.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 7.44 g (yield: 27%) of the expected product are obtained after purif... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1cccc(S)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be2199f40d44415e9d6c4b76de61d7c9 | CN(C)C(=S)Cl.Oc1ccccc1C(F)(F)F>>CN(C)C(=S)Oc1ccccc1C(F)(F)F | CN(C(=S)Cl)C.FC(C1=C(C=CC=C1)O)(F)F.[OH-].[K+]>>CN(C)C(=S)OC1=CC=CC=C1C(F)(F)F | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[S:5].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16]>>[CH3:1][N:2]([CH3:3])[C:4](=[S:5])[O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | CN(C)C(=S)Cl.Oc1ccccc1C(F)(F)F | CN(C)C(=S)Oc1ccccc1C(F)(F)F | null | null | null | Acylation | Schotten-Baumann to ester | 085dbfd01da3f23432eb68a0c9926226856f71cf39acf52aeac55f77c5219807 | 42727264d4762866b627891a642b01ccb211aee4f45c12cd2bb71e89549be2cf | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[S;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[S;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 89 | [{"value": 89.0, "product": "CN(C)C(=S)OC1=CC=CC=C1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation XI is followed starting from 3.95 g (24.3.10-3 mol) of 2-tri-fluoromethylphenol, 1.43 g (25.6.10-3 mol) of potassium hydroxide and 3.46 g (28.10-3 mol) of dimethylthiocarbamoyl chloride, 5.37 g (yield: 89%) of a yellow oil are obtained.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Thioamide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | null | null | null | CN(C)C(=S)Cl.Oc1ccccc1C(F)(F)F>>CN(C)C(=S)Oc1ccccc1C(F)(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b4d8de5548014418855293f67040f611 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C(F)(F)F)SC[C@H]1OC(C)=O | FC(C1=C(C=CC=C1)S)(F)F.[Hg](C#N)C#N.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[CH2:24][S:23]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:1... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccccc1S | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C(F)(F)F)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 34 | [{"value": 34.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=CC=C2)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 1.8 g (10.10-3 mol) of 2trifluoromethylbenzenethiol, 2.55 g (10.10-3 mol) of mercuric cyanide (Hg(CN)2) and 3.95 g (11.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.53 g (yield: 34%) of the expected product are obtained.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1ccccc1S>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C(F)(F)F)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b40073ab084446aca3ddff0719ca2133 | C[S-].N#Cc1ccc(-c2ccc(I)cc2)cc1>>N#Cc1ccc(-c2ccc(S)cc2)cc1 | IC1=CC=C(C=C1)C1=CC=C(C#N)C=C1.C[S-].[Na+]>>SC1=CC=C(C=C1)C1=CC=C(C#N)C=C1 | C[S-:11].I[c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:15][cH:14]2)[cH:13][cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([SH:11])[cH:12][cH:13]2)[cH:14][cH:15]1 | C[S-].N#Cc1ccc(-c2ccc(I)cc2)cc1 | N#Cc1ccc(-c2ccc(S)cc2)cc1 | null | null | CN(P(=O)(N(C)C)N(C)C)C | Heteroatom Alkylation and Arylation | OtherReaction | a68a9f190548bfb055191578c24b0de54c85f8443714e35747c2990bf0f973bd | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | c1ccc(-c2ccccc2)cc1 | C-[S-;H0;D1:1].I-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]>>[SH;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6] | 106.6 | [{"value": 106.6, "product": "SC1=CC=C(C=C1)C1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 3.25 g (10.8.10-3 mol) of 4-(4-iodophenyl)benzonitrile are dissolved in 50 ml of hexamethylphosphoramide, and 3.05 g (43.4.10-3 mol) of sodium thiomethylate are then added to the solution. The reaction mixture is heated at 100° C. for 1.5 hours and then, after cooling, hydrolyzed in a 1 N hydrochloric acid/ice mixture.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | CN(P(=O)(N(C)C)N(C)C)C | 100 | null | C[S-].N#Cc1ccc(-c2ccc(I)cc2)cc1>CN(P(=O)(N(C)C)N(C)C)C>N#Cc1ccc(-c2ccc(S)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5695140c336e4ddc99bfce8ba1baa852 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(-c2ccc(S)cc2)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O | SC1=CC=C(C=C1)C1=CC=C(C#N)C=C1.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:29]([O:30][C:31]([CH3:32])=[O:33])[CH2:28][S:27]1.[SH:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23][cH:24]2)[cH:25][cH:26]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(-c2ccc(S)cc2)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(-c2ccc(S[C@H]3CCCCS3)cc2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 10.2 | [{"value": 10.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.2, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | If the procedure described in Preparation I is followed starting from 2.3 g (10.9.10-3 mol) of 4-(4-mercaptophenyl)benzonitrile, 4.26 g (11.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 2.75 g (10.9.10-3 mol) of mercuric cyanide (Hg(CN)2), 0.540 g (yield: 10%) of the expected product is obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(-c2ccc(S)cc2)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37b7bb1ecdf94502af5f9622197b3b7e | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O>>N#Cc1ccc(-c2ccc(S[C@@H]3SC[C@@H](O)[C@H](O)[C@H]3O)cc2)cc1 | C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)C2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N | CC(=O)[O:16][C@@H:15]1[CH2:14][S:13][C@@H:12]([S:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23]3)[cH:22][cH:21]2)[C@H:19]([O:20]C(C)=O)[C@H:17]1[O:18]C(C)=O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([S:11][C@@H:12]3[S:13][CH2:14][C@@H:15]([OH:16])[C@H:17]([OH:18])[C@... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O | N#Cc1ccc(-c2ccc(S[C@@H]3SC[C@@H](O)[C@H](O)[C@H]3O)cc2)cc1 | null | null | null | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(-c2ccc(S[C@H]3CCCCS3)cc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 80 | [{"value": 80.0, "product": "S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation V is followed starting from 0.340 g (70.1.10-3 mol) of 4-(4-cyanophenyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 14a) and 17 ml of sodium methylate (8% w/v solution of Na in methanol), 0.200 g (yield: 80%) of the expected product is obtained after purifi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.c1ccccc1.C1CCSCC1 | HO- | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O>>N#Cc1ccc(-c2ccc(S[C@@H]3SC[C@@H](O)[C@H](O)[C@H]3O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-21012e4031214f1599ceb78ee6f4b6dc | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1cc(S)cc(C(F)(F)F)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cc(C(F)(F)F)cc(C(F)(F)F)c2)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.FC(C=1C=C(C=C(C1)C(F)(F)F)S)(F)F.[Hg](C#N)C#N.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:29]([O:30][C:31]([CH3:32])=[O:33])[CH2:28][S:27]1.[SH:12][c:13]1[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1cc(S)cc(C(F)(F)F)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cc(C(F)(F)F)cc(C(F)(F)F)c2)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 35.7 | [{"value": 35.7, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.5, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | null | null | If the procedure described in Preparation I is followed starting from 1.6 g (6.5.10-3 mol) of 3,5-bis(trifluoromethyl)benzenethiol, 1.64 g (6.5.10-3 mol) of mercuric cyanide, Hg(CN)2, and 2.54 g (7.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.2 g (yield: 35.7%) of the expected product are obtai... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.FC(F)(F)c1cc(S)cc(C(F)(F)F)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cc(C(F)(F)F)cc(C(F)(F)F)c2)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2500ab4f295340a7972ceb2a034d096d | C[S-].N#Cc1ccc(I)c(C#N)c1>>N#Cc1ccc(S)c(C#N)c1 | C(#N)C=1C=C(C#N)C=CC1I.C[S-].[Na+]>>C(#N)C=1C=C(C#N)C=CC1S | C[S-:7].I[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:11][c:8]1[C:9]#[N:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([SH:7])[c:8]([C:9]#[N:10])[cH:11]1 | C[S-].N#Cc1ccc(I)c(C#N)c1 | N#Cc1ccc(S)c(C#N)c1 | null | null | CN(P(=O)(N(C)C)N(C)C)C | Heteroatom Alkylation and Arylation | OtherReaction | a68a9f190548bfb055191578c24b0de54c85f8443714e35747c2990bf0f973bd | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | c1ccccc1 | C-[S-;H0;D1:1].I-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[c:8]>>[N;D1;H0:7]#[C:6]-[c:5](:[c:8]):[c;H0;D3;+0:2](-[SH;D1;+0:1]):[c:3]:[c:4] | 81 | [{"value": 81.0, "product": "C(#N)C=1C=C(C#N)C=CC1S", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Under argon, 3.03 g (12.10-3 mol) of 3-cyano-4-iodobenzonitrile and 3.36 g (48.10-3 mol) of sodium thiomethylate are dissolved in 80 ml of anhydrous hexamethylphosphoramide and the solution obtained is then heated at 80° C. for 45 minutes. The resulting reaction medium is hydrolyzed in an ice/1N HCl mixture and then ex... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | CN(P(=O)(N(C)C)N(C)C)C | 80 | null | C[S-].N#Cc1ccc(I)c(C#N)c1>CN(P(=O)(N(C)C)N(C)C)C>N#Cc1ccc(S)c(C#N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b55aa83528f442f49b35d1e8c285a53a | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)c(C#N)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.C(#N)C=1C=C(C#N)C=CC1S.[Hg](C#N)C#N.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[CH2:24][S:23]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][c:20]1[C:21]#[N:22]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)c(C#N)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 40.5 | [{"value": 40.5, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 1.5 g (9.10-3 mol) of 3-cyano-4-mercaptobenzonitrile, 2.78 g (11.10-3 mol) of mercuric cyanide, Hg(CN)2, and 3.66 g (11.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.65 g (yield: 40.5%) of the expected product are obtained.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)c(C#N)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d94fb37375fe483b836d9caf4ed1219f | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)c(C#N)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O | C(#N)C=1C=C(C#N)C=CC1S.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[CH2:24][S:23]1.[SH:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][c:20]1[C:21]#[N:22]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]2[cH:14][cH:15... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)c(C#N)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 47.9 | [{"value": 47.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 1.6 g (9.73.10-3 mol) of 3-cyano-4-mercaptobenzonitrile, 4.07 g (11.45.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 0.84 g (10.10-3 mol) of zinc oxide (ZnO), 2.08 g (yield: 47%) of the expected product are obtained.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(S)c(C#N)c1>[O-2].[Zn+2]>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ec9df3c100e1422cae944464b64f6d15 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O>>N#Cc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c(C#N)c1 | C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O>>S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=C(C=C1)C#N)C#N | CC(=O)[O:12][C@@H:11]1[CH2:10][S:9][C@@H:8]([S:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:20][c:17]2[C:18]#[N:19])[C@H:15]([O:16]C(C)=O)[C@H:13]1[O:14]C(C)=O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([S:7][C@@H:8]2[S:9][CH2:10][C@@H:11]([OH:12])[C@H:13]([OH:14])[C@H:15]2[OH:16])[c:17]([C:18]#[N:19])[cH:20]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O | N#Cc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c(C#N)c1 | null | null | C(Cl)Cl.CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(S[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 67 | [{"value": 67.0, "product": "S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=C(C=C1)C#N)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation V is followed, except that the reaction is carried out at 0° C., starting from 1.5 g (34.10-3 mol) of 2,4-dicyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 16a), 0.71 g (yield: 67%) of the expected product is obtained after chromatography on silica using a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | C(Cl)Cl.CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O>C(Cl)Cl.CO>N#Cc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c(C#N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-68057794265042cf843f66f80857944b | C[S-].N#Cc1cc(C#N)c(Br)c(C#N)c1>>N#Cc1cc(C#N)c(S)c(C#N)c1 | BrC1=C(C#N)C=C(C=C1C#N)C#N.C[S-].[Na+]>>C(#N)C=1C(=C(C#N)C=C(C1)C#N)S | C[S-:9].Br[c:8]1[c:5]([C:6]#[N:7])[cH:4][c:3]([C:2]#[N:1])[cH:13][c:10]1[C:11]#[N:12]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[c:8]([SH:9])[c:10]([C:11]#[N:12])[cH:13]1 | C[S-].N#Cc1cc(C#N)c(Br)c(C#N)c1 | N#Cc1cc(C#N)c(S)c(C#N)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a68a9f190548bfb055191578c24b0de54c85f8443714e35747c2990bf0f973bd | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]):[c:6](-[C:7]#[N;D1;H0:8]):[c:9].C-[S-;H0;D1:10]>>[N;D1;H0:4]#[C:3]-[c:2](:[c:5]):[c;H0;D3;+0:1](-[SH;D1;+0:10]):[c:6](-[C:7]#[N;D1;H0:8]):[c:9] | null | [] | null | null | null | null | If the procedure described in Preparation LV is followed starting from 6 g (26.10-3 mol) of 2-bromo-3,5-dicyanobenzonitrile and 6 g (86.10-3 mol) of sodium thiomethylate, 6 g (quantitative yield) of the expected product are obtained in the form of an oil.
Conditions: See reaction.notes.procedure_details.
Workup: If the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | null | null | C[S-].N#Cc1cc(C#N)c(Br)c(C#N)c1>>N#Cc1cc(C#N)c(S)c(C#N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-20ce36ae2e6848d387fd32a102b78617 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cc(C#N)c(S)c(C#N)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2c(C#N)cc(C#N)cc2C#N)SC[C@H]1OC(C)=O | C(#N)C=1C(=C(C#N)C=C(C1)C#N)S.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.[Hg](C#N)C#N>>C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2C#N)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:27]([O:28][C:29]([CH3:30])=[O:31])[CH2:26][S:25]1.[SH:12][c:13]1[c:14]([C:15]#[N:16])[cH:17][c:18]([C:19]#[N:20])[cH:21][c:22]1[C:23]#[N:24]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([S:12][c:13]... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cc(C#N)c(S)c(C#N)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2c(C#N)cc(C#N)cc2C#N)SC[C@H]1OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 17 | [{"value": 17.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=C(C=C(C=C2C#N)C#N)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation I is followed starting from 4.8 g (258.10-3 mol) of 3,5-dicyano-2-mercaptobenzonitrile (Example 17a), 9.71 g (258.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.57 g (8.6.10-3 mol) of mercuric cyanide (Hg(CN)2), 2 g (yield: 17%) of the expected product a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | null | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cc(C#N)c(S)c(C#N)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2c(C#N)cc(C#N)cc2C#N)SC[C@H]1OC(C)=O |
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